Imidazole → Benzyl 3-{[tert-butyl(dimethyl)silyl]oxy}cyclopentanecarboxylate

HRID 58875Notes

Reaction equation

HRID 58875 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].[OH:9][CH:10]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11]1.N1C=CN=C1.O>C1COCC1.CN(C=O)C>[Si:5]([O:9][CH:10]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[CH2:11]1)([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 14530758Benzyl 3-hydroxycyclopentanecarboxylate

Product 1

HCID 68717013Benzyl 3-{[tert-butyl(dimethyl)silyl]oxy}cyclopentanecarboxylateYield 101%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of TBSCl (7.5 g, 50 mmol) in THF (50 mL) was added dropwise to a solution of benzyl 3-hydroxycyclopentanecarboxylate (10.0 g, 45.0 mmol) and imidazole (3.4 g, 50 mmol) in DMF (100 mL) at ambient temperature. The reaction mixture was stirred for 3 h and water (300 mL) was added. The resulting mixture was extracted with EtOAc (200 mL×3). The combined organic extracts were washed with 5% aqueous KHSO4 (100 mL×3), saturated aqueous NaHCO3 (100 mL×3), and brine (100 mL×1), respectively. The organic solution was dried over anhydrous sodium sulfate, and concentrated to dryness. The residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:20) to afford benzyl 3-(tert-butyldimethylsilyloxy)cyclopentanecarboxylate (15.2 g, quantitative) as an oil.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (200 mL×3)
  2. washThe combined organic extracts were washed with 5% aqueous KHSO4 (100 mL×3), saturated aqueous NaHCO3 (100 mL×3), and brine (100 mL×1)
  3. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:20)

Sources & evidence

ORD record
ord-63318f004c614155b22c87b55210e082
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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