Methanol → (1S,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-(hydroxymethyl)cyclopentyl methanesulfonate

HRID 1747643Notes

Reaction equation

HRID 1747643 reaction equation
[CH3:1][S:2]([O:5][C@@H:6]1[CH2:10][C@H:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[C@H:8]([CH2:19][O:20]CC2C=CC=CC=2)[CH2:7]1)(=[O:4])=[O:3].CO>[OH-].[Pd+2].[OH-].[Pd]>[CH3:1][S:2]([O:5][C@H:6]1[CH2:7][C@@H:8]([CH2:19][OH:20])[C@@H:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:13])[CH3:14])[CH2:10]1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 887MethanolHCID 86618711(1S,3S,4S)-3-[(benzyloxy)methyl]-4-{[tert-butyl(dimethyl)silyl]oxy}cyclopentyl methanesulfonate

Product 1

HCID 86618728(1S,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-(hydroxymethyl)cyclopentyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalyst

Procedure

A suspension of (1S,3S,4S)-3-[(benzyloxy)methyl]-4-{[tert-butyl(dimethyl)silyl]-oxy}cyclopentyl methanesulfonate (690 mg, 0.0017 mol) and Palladium hydroxide, 20 wt. % Pd on carbon (160 mg, 0.00012 mol) in methanol (10 mL, 0.2 mol) was stirred under an atmosphere of hydrogen for 2 hours. The reaction was purged with nitrogen and filtered the mixture through celite with DCM. The filtrate was concentrated to obtain 350 mg (65%).

Workup

  1. customThe reaction was purged with nitrogen
  2. filtrationfiltered the mixture through celite with DCM
  3. concentrationThe filtrate was concentrated
  4. customto obtain 350 mg (65%)

Sources & evidence

ORD record
ord-9329c980bb6f44b2918b641ea59c8c82
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

Loading…