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

HRID 1243168Notes

Reaction equation

HRID 1243168 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b6eb1d08bb6c40439ddb712f6146802d
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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