(+)-(1S,3S)-(3-azido-cyclopentyloxy)-tert-butyl-dimethyl-silane → (+/-)-trans-3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentylamine

HRID 1243168ノート

反応式

HRID 1243168 の反応式
[N:1]([C@H:4]1[CH2:8][CH2:7][C@H:6]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH2:5]1)=[N+]=[N-].[H][H]>C(O)C.[Pt]=O>[C:13]([Si:10]([CH3:12])([CH3:11])[O:9][C@H:6]1[CH2:7][CH2:8][C@H:4]([NH2:1])[CH2:5]1)([CH3:16])([CH3:15])[CH3:14]

参加物

5

反応物 2

HCID 21062583(+)-(1S,3S)-(3-azido-cyclopentyloxy)-tert-butyl-dimethyl-silaneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 58715071(+/-)-trans-3-(Tert-butyl-dimethyl-silanyloxy)-cyclopentylamine

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 702Ethanol溶媒

実験手順

A mixture of (±)-trans-(3-azido-cyclopentyloxy)-tert-butyl-dimethyl-silane (400 mg, 1.66 mmol) (from Example 9b supra) and platinum oxide (38 mg, 0.17 mmol) (Aldrich) in ethanol (6 mL) was stirred under 1 atmosphere of hydrogen pressure for 2 hours. The reaction mixture was then filtered. The solids were washed with tetrahydrofuran (approx. 40 mL) and the combined organic layer was evaporated under reduced pressure to give (±)-trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentylamine as a colorless liquid. (Yield 270 mg, 76%).

後処理

  1. filtrationThe reaction mixture was then filtered
  2. washThe solids were washed with tetrahydrofuran (approx. 40 mL)
  3. customthe combined organic layer was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-b6eb1d08bb6c40439ddb712f6146802d
出典データセット
uspto-grants-2006_10
特許番号
US07115740B2

反応ノート

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