(3R,4R)-benzyl 3-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilyloxy)piperidine-1-carboxylate → tert-butyl (3R,4R)-4-(tert-butyldimethylsilyloxy)piperidin-3-ylcarbamate

HRID 1028071노트

반응식

HRID 1028071 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:14]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CCO.CCOC(C)=O>[Si:16]([O:15][C@@H:14]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

참가 물질

4

반응물 1

HCID 59455668(3R,4R)-benzyl 3-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilyloxy)piperidine-1-carboxylate

생성물 1

HCID 68922675tert-butyl (3R,4R)-4-(tert-butyldimethylsilyloxy)piperidin-3-ylcarbamate수율 99%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 21584252Ethanol ethylacetate용매

실험 절차

To a solution of (3R,4R)-benzyl 3-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsilyloxy)piperidine-1-carboxylate (1.0 equiv.) in 1:1 EtOH/EtOAc, at a concentration of 0.1 M, was added 10% palladium on carbon (0.1 eq.). The resultant heterogeneous solution was put under an atmosphere of hydrogen and was stirred for 72 hours. At this time the mixture was filtered through a pad of celite eluting with EtOAc. The volatiles were removed in vacuo yielding tert-butyl (3R,4R)-4-(tert-butyldimethylsilyloxy)piperidin-3-ylcarbamate (99%). LCMS (m/z): 331.3 (MH+).

후처리

  1. filtrationAt this time the mixture was filtered through a pad of celite
  2. washeluting with EtOAc
  3. customThe volatiles were removed in vacuo

출처 및 근거

ORD 기록
ord-a1b5d61ac92645c79d4850bfd4495980
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735424B2

반응 노트

불러오는 중…