Dimethylformamide → (2R,4R)-1-allyloxy-carbonyl-4-(t-butyldimethylsilyloxy)-2-[2-(1,2, 4-triazol-1-yl)ethyl]pyrrolidine

HRID 975712Notes

Reaction equation

HRID 975712 reaction equation
C(OC([N:7]1[CH2:11][C@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9][C@H:8]1[CH2:20][CH2:21]OS(C)(=O)=O)=O)C=C.[Na].[NH:28]1[CH:32]=[N:31][CH:30]=[N:29]1.CN(C)[CH:35]=[O:36]>>[CH2:10]([O:12][N:7]1[CH2:11][C@H:10]([O:12][Si:13]([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:14])[CH3:15])[C:9](=[C:35]=[O:36])[C@H:8]1[CH2:20][CH2:21][N:28]1[CH:32]=[N:31][CH:30]=[N:29]1)[CH:9]=[CH2:8]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 15537961(2R,4R)-1-allyloxycarbonyl-2-(2-methanesulfonyloxyethyl)-4-(t-butyldimethylsilyloxy)pyrrolidineHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 88372253(2R,4R)-1-allyloxy-carbonyl-4-(t-butyldimethylsilyloxy)-2-[2-(1,2, 4-triazol-1-yl)ethyl]pyrrolidine

Conditions

Temperature
60 °C

Procedure

A mixture of (2R,4R)-1-allyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(2-methanesulfonyloxyethyl)pyrrolidine (10.0 g) and 1,2,4-triazole sodium salt (2.45 g) in dimethylformamide (50 ml) was stirred at 60° C. for 3.5 hours. After cooling to room temperature, the mixture was quenched by the addition of water (100 ml) and extracted with a mixture of hexane and ethyl acetate (2:1, 50 ml×4). The combined extract was washed with water (400 ml), brine (100 ml) and dried over magnesium sulfate. Evaporation of the solvent gave (2R,4R)-1-allyloxy-carbonyl-4-(t-butyldimethylsilyloxy)-2-[2-(1,2, 4-triazol-1-yl)ethyl]pyrrolidine (8.82 g) as a light brown paste.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was quenched by the addition of water (100 ml)
  3. extractionextracted with a mixture of hexane and ethyl acetate (2:1, 50 ml×4)
  4. extractionThe combined extract
  5. washwas washed with water (400 ml), brine (100 ml)
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-dcdc03abcdc5414dacdc35e95acea9bf
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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