Imidazole → (-)-(1R,2S)-2-phenyl-1-cyclohexyl hydroxyacetate

HRID 487369

Reaction equation

HRID 487369 reaction equation
C([O:8][CH2:9][C:10](Cl)=[O:11])C1C=CC=CC=1.[C:13]1([C@@H:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]2[OH:25])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([Si](Cl)(C(C)C)C(C)C)(C)C.N1C=CN=C1>CN(C)C=O.CCCCC>[OH:11][CH2:10][C:9]([O:25][C@@H:20]1[CH2:21][CH2:22][CH2:23][CH2:24][C@H:19]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:8]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 102793rel-(1R,2S)-2-PhenylcyclohexanolHCID 139400Triisopropylsilyl chlorideHCID 177085Benzyloxyacetyl chloride

Product 1

HCID 10059921(-)-(1R,2S)-2-phenyl-1-cyclohexyl hydroxyacetateYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8003PentaneSolvent

Procedure

To obtain 1c(-), a solution of (-)-(1R,2S)-2-phenyl-1-cyclohexyl hydroxyacetate (851 mg, 3.63 mmol) was prepared through esterification of benzyloxyacetyl chloride with (-)-(1R,2S)-2-phenyl-1-cyclohexanol followed by hydrogenolysis. Then, triisopropylsilyl chloride (840 mg, 4.36 mmol) and imidazole (618 mg, 9.08 mmol) in dimethylformamide (DMF) (1.7 mL) was stirred at room temperature for 12-20 hours. The mixture was poured into pentane (25 mL), and washed with water and brine. The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was subjected to a purification on a short silica gel column using hexane/chloroform (3/1) as the eluant to give pure 1c(-) (1.35 g, 95% yield) as a colorless oil.

Workup

  1. customTo obtain 1c(-)
  2. washwashed with water and brine
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was subjected to a purification on a short silica gel column
  6. customto give pure 1c(-) (1.35 g, 95% yield) as a colorless oil

Sources & evidence

ORD record
ord-8c8b239c359f4197a5536012d4027c08
Source dataset
uspto-grants-1994_03
Patent number
US05294737

Linked notes

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