Synthesis

Reductive One Batch Synthesis of N-Substituted Pyrrolidines from Primary Amines and 2, 5-Dimethoxytetrahydrofuran

G Verardo, A Dolce, N Toniutti

Index: Verardo, Giancarlo; Dolce, Anna; Toniutti, Nicoletta Synthesis, 1999 , # 1 p. 74 - 79

Full Text: HTML

Citation Number: 10

Abstract

Abstract: The construction of the pyrrolidine ring about a nitrogen of a primary amine by a reductive condensation reaction using 2, 5-dimethoxytetrahydrofuran and sodium borohydride in acidic water medium is described. The reaction is fast, affords good to excellent yields and appears insensitive to electron effects and severe steric hindrance; it is found to be compatible with a large variety of aryl substituents, including nitro and oxo ...

 Related Synthetic Route
2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

Cyclohexylamine Structure

108-91-8

Cyclohexylamine

~36%

1-CYCLOHEXYL-PYRROLIDINE Structure

7731-02-4

1-CYCLOHEXYL-PY...

1-cyclohexyl-1H-Pyrrole Structure

31708-14-2

1-cyclohexyl-1H...

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2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

o-Toluidine Structure

95-53-4

o-Toluidine

~81%

1H-PYRROLE, 1-(2-METHYLPHENYL) Structure

2437-42-5

1H-PYRROLE, 1-(...

PYRROLIDINE, 1-(2-METHYLPHENYL) Structure

41378-30-7

PYRROLIDINE, 1-...

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2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

4-Aminoacetophenone Structure

99-92-3

4-Aminoacetophenone

~0%

1-(4-(1H-Pyrrol-1-yl)phenyl)ethanone Structure

22106-37-2

1-(4-(1H-Pyrrol...

4-(1-PYRROLIDINO)ACETOPHENONE Structure

21557-09-5

4-(1-PYRROLIDIN...

Learn More
2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

Benzylamine Structure

100-46-9

Benzylamine

~38%

N-Benzylpyrrole Structure

2051-97-0

N-Benzylpyrrole

1-benzylpyrrolidine Structure

29897-82-3

1-benzylpyrrolidine

Learn More
2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

3-Toluidine Structure

108-44-1

3-Toluidine

~0%

1H-Pyrrole,1-(3-methylphenyl) Structure

2437-43-6

1H-Pyrrole,1-(3...

PYRROLIDINE, 1-(3-METHYLPHENYL) Structure

71982-22-4

PYRROLIDINE, 1-...

Learn More
2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

p-Anisidine Structure

104-94-9

p-Anisidine

~0%

1H-Pyrrole,1-(4-methoxyphenyl) Structure

5145-71-1

1H-Pyrrole,1-(4...

1-(4-Methoxyphenyl)pyrrolidine Structure

54660-04-7

1-(4-Methoxyphe...

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2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

4-Nitroaniline Structure

100-01-6

4-Nitroaniline

~0%

1H-Pyrrole,1-(4-nitrophenyl) Structure

4533-42-0

1H-Pyrrole,1-(4...

1-(4-Nitrophenyl)pyrrolidine Structure

10220-22-1

1-(4-Nitropheny...

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2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

4-Chloroaniline Structure

106-47-8

4-Chloroaniline

~88%

1-(4-Chlorophenyl)pyrrole Structure

5044-38-2

1-(4-Chlorophen...

PYRROLIDINE, 1-(4-CHLOROPHENYL) Structure

4280-30-2

PYRROLIDINE, 1-...

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2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

p-Anisidine Structure

104-94-9

p-Anisidine

~83%

1H-Pyrrole,1-(4-methoxyphenyl) Structure

5145-71-1

1H-Pyrrole,1-(4...

1-(4-Methoxyphenyl)pyrrolidine Structure

54660-04-7

1-(4-Methoxyphe...

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2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

2-Nitroaniline Structure

88-74-4

2-Nitroaniline

~0%

1-(2-NITRO-PHENYL)-3-PHENYL-PIPERAZINE Structure

33265-60-0

1-(2-NITRO-PHEN...

1-(2-Nitrophenyl)pyrrolidine Structure

40832-79-9

1-(2-Nitropheny...

Learn More
2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

4-Aminoacetophenone Structure

99-92-3

4-Aminoacetophenone

~87%

1-(4-(1H-Pyrrol-1-yl)phenyl)ethanone Structure

22106-37-2

1-(4-(1H-Pyrrol...

4-(1-PYRROLIDINO)ACETOPHENONE Structure

21557-09-5

4-(1-PYRROLIDIN...

Learn More
2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

Structure

74497-02-2

~87%

1-Phenylpyrrole Structure

635-90-5

1-Phenylpyrrole

1-Phenylpyrrolidine Structure

4096-21-3

1-Phenylpyrrolidine

Learn More
2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

p-Toluidine Structure

106-49-0

p-Toluidine

~0%

1H-Pyrrole,1-(4-methylphenyl) Structure

827-60-1

1H-Pyrrole,1-(4...

PYRROLIDINE, 1-(4-METHYLPHENYL) Structure

54104-82-4

PYRROLIDINE, 1-...

Learn More
2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

4-Chloroaniline Structure

106-47-8

4-Chloroaniline

~0%

1-(4-Chlorophenyl)pyrrole Structure

5044-38-2

1-(4-Chlorophen...

PYRROLIDINE, 1-(4-CHLOROPHENYL) Structure

4280-30-2

PYRROLIDINE, 1-...

Learn More
2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

3-anisidine Structure

536-90-3

3-anisidine

~78%

PYRROLIDINE, 1-(3-METHOXYPHENYL) Structure

32040-07-6

PYRROLIDINE, 1-...

1H-Pyrrole,1-(3-methoxyphenyl)-(9CI) Structure

188953-77-7

1H-Pyrrole,1-(3...

Learn More
2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

p-Toluidine Structure

106-49-0

p-Toluidine

~84%

1H-Pyrrole,1-(4-methylphenyl) Structure

827-60-1

1H-Pyrrole,1-(4...

PYRROLIDINE, 1-(4-METHYLPHENYL) Structure

54104-82-4

PYRROLIDINE, 1-...

Learn More
2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

Structure

74497-02-2

~0%

1-Phenylpyrrole Structure

635-90-5

1-Phenylpyrrole

1-Phenylpyrrolidine Structure

4096-21-3

1-Phenylpyrrolidine

Learn More
2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

Benzylamine Structure

100-46-9

Benzylamine

~0%

N-Benzylpyrrole Structure

2051-97-0

N-Benzylpyrrole

1-benzylpyrrolidine Structure

29897-82-3

1-benzylpyrrolidine

Learn More
2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

2-Nitroaniline Structure

88-74-4

2-Nitroaniline

~65%

1-(2-NITRO-PHENYL)-3-PHENYL-PIPERAZINE Structure

33265-60-0

1-(2-NITRO-PHEN...

1-(2-Nitrophenyl)pyrrolidine Structure

40832-79-9

1-(2-Nitropheny...

Learn More
2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

3-anisidine Structure

536-90-3

3-anisidine

~0%

PYRROLIDINE, 1-(3-METHOXYPHENYL) Structure

32040-07-6

PYRROLIDINE, 1-...

1H-Pyrrole,1-(3-methoxyphenyl)-(9CI) Structure

188953-77-7

1H-Pyrrole,1-(3...

Learn More
2,5-Dimethoxytetrahydrofuran Structure

696-59-3

2,5-Dimethoxyte...

3-Bromoaniline Structure

591-19-5

3-Bromoaniline

~0%

1-(3-Bromophenyl)-1H-pyrrole Structure

107302-22-7

1-(3-Bromopheny...

1-(3-Bromophenyl)pyrrolidine Structure

219928-13-9

1-(3-Bromopheny...

Learn More

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