(2S,3R)-1-tert-Butoxycarbonyl-3-(3-hydroxypropyn-1-yl)-2-phenylpiperidin-3-ol → Z-(2S,3R)-1-tert-Butoxycarbonyl-3-(3-hydroxyprop-1-en-1-yl)-2-phenylpiperidin-3-ol

HRID 565375

반응식

HRID 565375 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@:10]([C:15]#[C:16][CH2:17][OH:18])([OH:14])[C@@H:9]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@:10](/[CH:15]=[CH:16]\[CH2:17][OH:18])([OH:14])[C@@H:9]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 1

HCID 11301992(2S,3R)-1-tert-Butoxycarbonyl-3-(3-hydroxypropyn-1-yl)-2-phenylpiperidin-3-ol

생성물 1

HCID 59038479Z-(2S,3R)-1-tert-Butoxycarbonyl-3-(3-hydroxyprop-1-en-1-yl)-2-phenylpiperidin-3-ol수율 100%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 131709914Lindlars catalyst촉매HCID 8857Ethyl Acetate용매

실험 절차

Palladium on calcium carbonate, poisoned with lead (Lindlar catalyst, 2 g) was added to a solution of (2S,3R)-1-tert-butoxycarbonyl-3-(3-hydroxypropyn-1yl)-2-phenylpiperidin-3-ol (Description 2; 32 g, 96.6 mmol) in ethyl acetate (300 ml) and the mixture was stirred under hydrogen (1 atmosphere) for 4 hours. The mixture was filtered and the solvent was evaporated under reduced pressure to give the title compound as an oil (32 g, 100%). 1H NMR (360 MHz, CDCl3) δ 7.42 (2H, d, J 7.6 Hz), 7.35−7.25 (3H, m), 5.83 (1H, d, J 12.3 Hz), 5.68 (1H, dt, J 12.3, 6.0 Hz), 5.06 (1H, s), 4.27 (1H, m), 4.12 (2H, m), 3.32 (1H, m), 3.13 (1H, s), 2.28 (1H, t, J 5.9 Hz), 2.02 (1H, m), 1.92−1.78 (3H, m), and 1.32 (9H, s). m/z (ES+) 334 (M+1).

후처리

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-8015db31df6340149d12302d04bc21c5
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172077B2

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