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

HRID 1243208Notes

Reaction equation

HRID 1243208 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]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].C1(C)C=CC=CC=1>[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, compound

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 1140TolueneSolvent

Procedure

A solution of (+)-(1S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enol (1.43 g, 6.67 mmol) (from Example 29a supra) and Wilkinson's catalyst (1.23 g, 1.33 mmol) (Aldrich) in toluene (55 mL) was subjected to atmospheric pressure hydrogenation for 16.5 hours. The reaction mixture was then filtered, concentrated to a small volume, and purified by silica gel column chromatography with a 0–25% ethyl acetate in hexanes gradient to give (+)-(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol as a colorless oil. (Yield 745 mg, 61%).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated to a small volume
  3. custompurified by silica gel column chromatography with a 0–25% ethyl acetate in hexanes gradient

Sources & evidence

ORD record
ord-681f15629df742b88e6fee5ad0b13ded
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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