Imidazole → HCID 15117255, compound

HRID 1029640Notes

Reaction equation

HRID 1029640 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][OH:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:28](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29].[Cl-].[Na+]>ClCCl.O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 5234Sodium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 15117254Phenylmethyl (2S,4R)-2-(hydroxymethyl)-4-[(methylsulfonyl)oxy]-1-pyrrolidinecarboxylate

Product 1

HCID 15117255HCID 15117255, compoundYield 87.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine (60 g) and imidazole (12.9 g) in dichloromethane (300 ml) was added dropwise a solution of tert-butyldimethylsilyl chloride (31.4 g) in dichloromethane at 0° C. over a 30-minute period. After one hour, the reaction mixture was poured into a mixture of ethyl acetate (1 l), water (400 ml) and saturated aqueous sodium chloride (200 ml). The organic layer was separated, washed in turn with water and brine, and dried over magnesium sulfate. Evaporation of the solvent gave an oil, which was chromatographed on silica gel (1.2 l) eluting with a mixture of hexane and ethyl acetate (1:1 V/V) to give (2S,4R)-1-benzyloxycarbonyl-2-(tert-butyldimethylsilyloxy)methyl-4-methanesulfonyloxypyrrolidine (71 g).

Workup

  1. customThe organic layer was separated
  2. washwashed in turn with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent
  5. customgave an oil, which
  6. customwas chromatographed on silica gel (1.2 l)
  7. washeluting with a mixture of hexane and ethyl acetate (1:1 V/V)

Sources & evidence

ORD record
ord-d9814ad4622947afb6ea05dfb6e152c8
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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