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

HRID 1747645Notes

Reaction equation

HRID 1747645 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-4f3b7000179e4c40ac84d015e6cb2c5a
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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