1-Azido-5-{[tert-butyl(dimethyl)silyl]oxy}-3-phenylpentan-3-ol → 1-Amino-5-{[tert-butyl(dimethyl)silyl]oxy}-3-phenylpentan-3-ol

HRID 271992Notes

Reaction equation

HRID 271992 reaction equation
[N:1]([CH2:4][CH2:5][C:6]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([OH:17])[CH2:7][CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[N+]=[N-]>CCOC(C)=O.[Pd]>[NH2:1][CH2:4][CH2:5][C:6]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([OH:17])[CH2:7][CH2:8][O:9][Si:10]([C:13]([CH3:14])([CH3:15])[CH3:16])([CH3:11])[CH3:12]

Participants

4

Reactant 1

HCID 598359641-Azido-5-{[tert-butyl(dimethyl)silyl]oxy}-3-phenylpentan-3-ol

Product 1

HCID 598359811-Amino-5-{[tert-butyl(dimethyl)silyl]oxy}-3-phenylpentan-3-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-azido-5-{[tert-butyl(dimethyl)silyl]oxy}-3-phenylpentan-3-ol (1.19, 3.3 mmol) in 30 mL EtOAc was stirred for 2 h under 40 psi of H2 gas in the presence of catalytic 10% Pd/C. After filtration through celite, the reaction mixture was evaporated to give 1-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-3-phenylpentan-3-ol in quantitative yield as a clear oil that was used without further purification. ESI-MS 310 (M+H), 332 (M+Na).

Workup

  1. filtrationAfter filtration through celite
  2. customthe reaction mixture was evaporated

Sources & evidence

ORD record
ord-99a40821f1ac4a24862acd2a8654ca72
Source dataset
uspto-grants-2008_11
Patent number
US07452992B2

Reaction notes

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