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 245067ノート

反応式

HRID 245067 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b97ab8e8c7bb43a68dfd9e2deeb76cf8
出典データセット
uspto-grants-2014_02
特許番号
US08658693B2

反応ノート

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