Imidazole → (1S,3R)-3-{[tert-Butyl(dimethyl)silyl]oxy}cyclopentan-1-ol

HRID 1243170Notes

Reaction equation

HRID 1243170 reaction equation
[CH:1]1([OH:7])[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.N1C=CN=C1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>O1CCCC1>[C:16]([Si:13]([CH3:15])([CH3:14])[O:6][C@H:3]1[CH2:4][CH2:5][C@H:1]([OH:7])[CH2:2]1)([CH3:19])([CH3:18])[CH3:17].[C:16]([Si:13]([CH3:15])([CH3:14])[O:6][C@@H:3]1[CH2:4][CH2:5][C@H:1]([OH:7])[CH2:2]1)([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 100165Cyclopentane-1,3-diol

Product 2

HCID 54118351(1S,3R)-3-{[tert-Butyl(dimethyl)silyl]oxy}cyclopentan-1-olYield 11.3%HCID 58715064Cyclopentanol, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, trans-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1,3-cyclopentanediol (5.0 g, 48.9 mmol) (cis/trans mixture, Aldrich) and imidazole (3.3 g, 48.5 mmol) in tetrahydrofuran (100 mL) at 0° C. was added tert-butyldimethylsilyl chloride (5.2 g, 34.3 mmol) (Aldrich) in portions (250 mg every 15 minutes). When all additions were completed the reaction mixture was allowed to slowly warn to room temperature. After stirring overnight the mixture was partitioned between ethyl acetate and water. The organic layer was collected, dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography on a silica gel column with a 0–20% ethyl acetate in hexanes gradient to give (±)-trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol as a colorless viscous oil, (Yield 4.23 g, 57%), and (±)-cis-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol (Yield 420 mg, 6%).

Workup

  1. customto slowly warn to room temperature
  2. customwas partitioned between ethyl acetate and water
  3. customThe organic layer was collected
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on a silica gel column with a 0–20% ethyl acetate in hexanes gradient

Sources & evidence

ORD record
ord-94749dc3ddea4b95b2cf314163ee81f8
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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