Imidazole → HCID 15117258, compound

HRID 1029642Notes

Reaction equation

HRID 1029642 reaction equation
[C:1]([CH:4]1[CH2:8][N:7]([C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[C@H:6]([CH2:15][OH:16])[CH2:5]1)(=[O:3])[CH3:2].N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>ClCCl>[C:1]([CH:4]1[CH2:8][N:7]([C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[C@H:6]([CH2:15][O:16][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 15117257HCID 15117257, compound

Product 1

HCID 15117258HCID 15117258, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2S)-4-acetyl-1-allyloxycarbonyl-2-hydroxymethylpyrrolidine (2.14 g) and imidazole (770 mg) in dichloromethane (20 ml) was added dropwise a solution of tert-butyldimethylsilyl chloride (1.7 g) in dichloromethane (5 ml) at 0° C. After one hour, the reaction mixture was washed in turn with 1N-hydrochloric acid and brine, and dried over magnesium sulfate. Evaporation of the solvent gave an oil, which was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (2:1, V/V) to give (2S)-4-acetyl-1-allyloxycarbonyl-2-(tert-butyldimethylsilyloxy)methylpyrrolidine (2.725 g).

Workup

  1. washthe reaction mixture was washed in turn with 1N-hydrochloric acid and brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of the solvent
  4. customgave an oil, which
  5. customwas chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (2:1, V/V)

Sources & evidence

ORD record
ord-d1b588f6ee714f4898bb2c6dd2059f86
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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