2-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, cis- → (1S,3R)-3-{[tert-Butyl(dimethyl)silyl]oxy}cyclopentan-1-ol

HRID 2393908Notes

Reaction equation

HRID 2393908 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:13][C@H:12]([OH:14])[CH:11]=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H][H]>CO>[Si:1]([O:8][C@@H:9]1[CH2:10][CH2:11][C@H:12]([OH:14])[CH2:13]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 101767472-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, cis-HCID 178418361HCID 178418361, compound

Product 1

HCID 54118351(1S,3R)-3-{[tert-Butyl(dimethyl)silyl]oxy}cyclopentan-1-olYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Combine (+/-)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol (2.50 g, 11.6 mmol, prepared in example 3) and Ni2B (8.5 mL of a 0.14M slurry in methanol, 10 mol %) in methanol (14 mL). Stir the slurry under an atmosphere of hydrogen for 18.5 hours. Then replace the hydrogen atmosphere with nitrogen, filter through diatomaceous earth and rinse the solids with methanol (50 mL). Concentrate the filtrate under vacuum (15 mmHg/40° C.) and purify the residue by Kugelrohr distillation (0.6 mmHg/60°-65° C.) to provide the title compound as a colorless oil (2.31 g, 92%).

Workup

  1. filtrationfilter through diatomaceous earth
  2. washrinse the solids with methanol (50 mL)
  3. concentrationConcentrate the filtrate under vacuum (15 mmHg/40° C.)
  4. custompurify the residue
  5. distillationby Kugelrohr distillation (0.6 mmHg/60°-65° C.)

Sources & evidence

ORD record
ord-3e0590116897458c994c9ab52fa66d66
Source dataset
uspto-grants-1998_09
Patent number
US05808112

Reaction notes

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