Benzyl trans(+/-)-4-[(tert-butoxycarbonyl)amino]-3-{[tert-butyl(dimethyl)silyl]oxy}piperidine-1-carboxylate → tert-Butyl (trans(+/-)-3-{[tert-butyl(dimethyl)silyl]oxy}piperidin-4-yl)carbamate

HRID 1430813노트

반응식

HRID 1430813 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][N:12](C(OCC2C=CC=CC=2)=O)[CH2:11][C@H:10]1[O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[Si:26]([O:25][C@H:10]1[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][CH2:13][NH:12][CH2:11]1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]

참가 물질

4

반응물 1

HCID 60200764Benzyl trans(+/-)-4-[(tert-butoxycarbonyl)amino]-3-{[tert-butyl(dimethyl)silyl]oxy}piperidine-1-carboxylate

생성물 1

HCID 60200917tert-Butyl (trans(+/-)-3-{[tert-butyl(dimethyl)silyl]oxy}piperidin-4-yl)carbamate수율 95%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A mixture of (+/−)-(3R,4R)-benzyl 4-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)piperidine-1-carboxylate (13 g, 28.0 mmol) and Pd/C (5% on carbon, 1.786 g, 0.839 mmol) in methanol (250 mL) was hydrogenated at 30 psi overnight. The mixture was filtered through Celite and the filtrate was concentrated in vacuo and further dried under high vacuum at 40° C. overnight. The crude product was used without purification. (+/−)-tert-butyl ((3R,4R)-3-((tert-butyldimethylsilyl)oxy)piperidin-4-yl)carbamate (8.8 g, 26.6 mmol, 95% yield) was obtained as a white solid.

후처리

  1. customwas hydrogenated at 30 psi overnight
  2. filtrationThe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customfurther dried under high vacuum at 40° C. overnight
  5. customThe crude product was used without purification

출처 및 근거

ORD 기록
ord-c235ee6d722841838ed611ea6b6fe686
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940736B2

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