Ethyl Acetate → ((1S,2S,4R)-4-amino-2-{[tert-butyl(dimethyl)silyl]oxy}cyclopentyl)methanol

HRID 447651Notes

Reaction equation

HRID 447651 reaction equation
[N:1]([C@@H:4]1[CH2:8][C@@H:7]([CH2:9][OH:10])[C@@H:6]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:5]1)=[N+]=[N-].CCOC(C)=O>[Pd]>[NH2:1][C@@H:4]1[CH2:8][C@@H:7]([CH2:9][OH:10])[C@@H:6]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:13])[CH3:14])[CH2:5]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 59671297((1S,2S,4R)-4-azido-2-{[tert-butyl(dimethyl)silyl]oxy}cyclopentyl)methanol

Product 1

HCID 59671329((1S,2S,4R)-4-amino-2-{[tert-butyl(dimethyl)silyl]oxy}cyclopentyl)methanolYield 87.6%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of ((1S,2S,4R)-4-azido-2-{[tert-butyl(dimethyl)silyl]oxy}-cyclopentyl)methanol (0.211 g, 0.000777 mol) and 10% Pd/C (0.047 g, 0.000044 mol) in EtOAc (6 mL, 0.06 mol) was stirred under an atmosphere of Hydrogen overnight. The reaction was purged with nitrogen and filtered the mixture through celite with DCM. The filtrate was concentrated to obtain 167 mg (87.5%) of the title compound.

Workup

  1. customThe reaction was purged with nitrogen
  2. filtrationfiltered the mixture through celite with DCM
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-99994a0e3fd840788797bb7b8ad94a88
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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