rel-(1S,2R,5S)-2-azido-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol → rel-(1S,2R,5S)-2-Amino-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol

HRID 245067노트

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HRID 245067 반응식
[N:1]([C@@H:4]1[CH2:8][CH2:7][C@H:6]([O:9][Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@@:5]1([CH3:28])[OH:27])=[N+]=[N-]>[Pd].C(O)C>[NH2:1][C@@H:4]1[CH2:8][CH2:7][C@H:6]([O:9][Si:10]([C:23]([CH3:25])([CH3:24])[CH3:26])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@:5]1([CH3:28])[OH:27]

참가 물질

4

반응물 1

HCID 86693778rel-(1S,2R,5S)-2-azido-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol

생성물 1

HCID 86693777rel-(1S,2R,5S)-2-Amino-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol수율 20%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A mixture of rel-(1S,2R,5S)-2-azido-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol (2.28 g, 5.76 mmol, enantiomeric mixture) and 10% palladium on carbon (61 mg) in ethanol (29 mL) is hydrogenated (60 psi) at room temperature for 16 h. The reaction is filtered through a pad of diatomaceous earth and rinsed with EtOH (50 mL). The filtrate is concentrated in vacuo, dissolved in dichloromethane (10 mL), and concentrated in vacuo. The crude product is purified on silica gel (120 g, 1-6% (2 M ammonia in methanol/dichloromethane) to afford the title compound as an opaque yellow oil (419 mg, 20%). LC-ES/MS m/z 353 (M+1).

후처리

  1. customat room temperature
  2. customfor 16 h
  3. filtrationThe reaction is filtered through a pad of diatomaceous earth
  4. washrinsed with EtOH (50 mL)
  5. concentrationThe filtrate is concentrated in vacuo
  6. dissolutiondissolved in dichloromethane (10 mL)
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified on silica gel (120 g, 1-6% (2 M ammonia in methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-b97ab8e8c7bb43a68dfd9e2deeb76cf8
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658693B2

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