HCID 18759322, compound → (2R 3S)-N-[(tert-butyloxy)carbonyl]-3-amino-2-(triisopropylsilyloxy)-4-cyclohexyl-1-butanol

HRID 1729059Notes

Reaction equation

HRID 1729059 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:10]([O:13][Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])[CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:24][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1)[C@@H:10]([O:13][Si:14]([CH:15]([CH3:16])[CH3:17])([CH:18]([CH3:19])[CH3:20])[CH:21]([CH3:22])[CH3:23])[CH2:11][OH:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 18759322HCID 18759322, compound

Product 1

HCID 15281983(2R 3S)-N-[(tert-butyloxy)carbonyl]-3-amino-2-(triisopropylsilyloxy)-4-cyclohexyl-1-butanolYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The monosilylated diol of Step 2 was hydrogenated with 5% Rh-C at 60 psi and 60° C. in MeOH (135 mL). The mixture was filtered and the filtrate evaporated. The residue was purified by chromatography, eluting with (15% EtOAc in hexane) to give the title alcohol (8.70 g, 67% yield, mp 61°-63° C). The 1H, 13C, and APT NMR spectral data were consistent with the proposed product.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. customThe residue was purified by chromatography
  4. washeluting with (15% EtOAc in hexane)

Sources & evidence

ORD record
ord-636edb0ddd164e358d31523c83780c92
Source dataset
uspto-grants-1994_07
Patent number
US05330996

Reaction notes

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