Imidazole → (1S,3S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentanol

HRID 1677941Notes

Reaction equation

HRID 1677941 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4]1.N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C=O)C>[Si:14]([O:1][CH2:2][C@H:3]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride2×HCID 586511153-(Hydroxymethyl)cyclopentanol

Product 1

HCID 66797963(1S,3S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentanolYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1S,3S)-3-(hydroxymethyl)cyclopentanol (453.0 mg, 0.003276 mol) and 1H-imidazole (669 mg, 0.00983 mol) in DMF (35.8 mL) under an atmosphere of nitrogen was added tert-butyldimethylsilyl chloride (494 mg, 0.00328 mol). The mixture was stirred for 1.25 hours, then tert-butyldimethylsilyl chloride (49 mg, 0.00033 mol) was added. After an additional hour of stirring, the reaction was quenched with water, extracted with ethyl acetate (3×), dried with anhydrous Na2SO4, filtered, and concentrated. The residue was filtered through a plug of silica with 30% EtOAc/hexanes to obtain 234.1 mg (31%) of the title compound.

Workup

  1. stirringAfter an additional hour of stirring
  2. customthe reaction was quenched with water
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialdried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationThe residue was filtered through a plug of silica with 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-ce3c0f8818d44e0c92ed64ebf8c21344
Source dataset
uspto-grants-2011_08
Patent number
US08008307B2

Reaction notes

Loading…