Enantioselective synthesis of (S)-5-aminopiperidin-2-one from (S)-pyroglutaminol

SK Panday, N Langlois

Index: Panday, Sharad Kumar; Langlois, Nicole Tetrahedron Letters, 1995 , vol. 36, # 45 p. 8205 - 8208

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Citation Number: 10

Abstract

9 : mp : 98-9 °C ; [α] D 23 − 16 (c 0.98, CHCl 3 ) ; IR (CHCl 3 , v cm-1) : 3448, 3037, 2957, 1722 (broad), 1616, 1529; 1 H NMR [300 MHz, C 6 D 6 , δ = 0: TMS, J (Hz)] : 7.25, 7.10 (5H, Ar-H), 5.05 (s, 2H, OCH 2 Ph), 4.88 (bs, NH), 3.64 (bs, 1H, H-4), 3.41 (s, 3H, CO 2 CH 3 ), 3.31 (s, 3H, CO 2 CH 3 ), 2.94 (m, 2H, NCH 2 ), 2.10 (m, 2H, H 2 -2), 1.52 (m, 2H, H 2 -3). 13 C NMR (75 MHz) : 174.17 (CO), 157.88 (NCO 2 ), 156.70 (NCO 2 ), 136.51 ...