Imidazole → HCID 57258684, compound

HRID 1613986Notes

Reaction equation

HRID 1613986 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])[C@H:11]([CH2:27]I)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>>[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])[C@:11]([CH3:27])([N:29]2[CH:33]=[CH:32][N:31]=[CH:30]2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 795ImidazoleHCID 15537960HCID 15537960, compound

Product 1

HCID 57258684HCID 57258684, compoundYield 59.1%

Procedure

A mixture of (2S,4R)-4-t-butyldimethylsilyloxy-2-iodomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (3.00 g) and imidazole (15.0 g) was fused at 100-110° C. for 5 hours with stirring. The mixture was poured into ice-water (150 ml) and extracted with chloroform (50 ml ×3). The organic layers were combined, washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (30 g) and eluted with a mixture of methanol and chloroform (1:99, V/V) to give (2S,4R)-4-t-butyldimethylsilyloxy-2-(imidazol-1-yl)-methyl-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (1.57 g).

Workup

  1. extractionextracted with chloroform (50 ml ×3)
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a syrup
  6. washeluted with a mixture of methanol and chloroform (1:99, V/V)

Sources & evidence

ORD record
ord-c6e156a5e1c149a38914b062d84c6d54
Source dataset
uspto-grants-1993_03
Patent number
US05194624

Reaction notes

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