Ethyl Acetate → (1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentanamine

HRID 447695Notes

Reaction equation

HRID 447695 reaction equation
[N:1]([C@@H:4]1[CH2:8][C@@H:7]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[C@@H:6]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:5]1)=[N+]=[N-].CCOC(C)=O>[Pd]>[Si:19]([O:18][C@@H:6]1[C@H:7]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:12])[CH3:13])[CH2:8][C@@H:4]([NH2:1])[CH2:5]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 86618737[((1S,2S,4R)-4-azido-2-{[tert-butyl(dimethyl)silyl]oxy}cyclopentyl)methoxy](tert-butyl)dimethylsilane

Product 1

HCID 59671204(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentanamineYield 92.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of [((1S,2S,4R)-4-azido-2-{[tert-butyl(dimethyl)silyl]oxy}-cyclopentyl)methoxy](tert-butyl)dimethylsilane (2.13 g, 0.00552 mol) and 10% Pd/C (0.27 g, 0.00026 mol) in EtOAc (45.0 mL, 0.461 mol) was stirred under an atmosphere of hydrogen overnight. The reaction was purged with nitrogen and filtered the mixture through celite with EtOAc. The filtrate was concentrated to obtain 1.83 g (92.1%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-84f24c78e93f48318def49b0d2a37cbc
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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