2-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, cis- → HCID 23550265, compound

HRID 402532Notes

Reaction equation

HRID 402532 reaction equation
[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][C@@H:7]1[CH2:11][C@H:10]([OH:12])[CH:9]=[CH:8]1)([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][C@H:7]1[CH2:8][CH2:9][C@@H:10]([OH:12])[CH2:11]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 101767472-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, cis-

Product 1

HCID 23550265HCID 23550265, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.0 g (9.33 mmol) of (1S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enol (Curran, et al. Tetrahedron 1997, 53, 1983-2004) in 10 mL of ethyl acetate was treated with 66 mg of 20% palladium hydroxide on activated carbon and the mixture was stirred overnight under a hydrogen atmosphere (1 atm) at room temperature. The catalyst was removed by filtration, and the filtrate was evaporated in vacuo to give 2.0 g of the title compound (32). Rt=1.72 min (Method C). Detected mass: 217.2 (M+H+).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-254c0bb0502e4f418912a371fd44c0c0
Source dataset
uspto-grants-2014_06
Patent number
US08742116B2

Reaction notes

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