Ammonium Chloride → (2S,4S)-1-allyloxycarbonyl-4-azido-2-hydroxymethylpyrrolidine

HRID 1090506Notes

Reaction equation

HRID 1090506 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10](OS(C)(=O)=O)[CH2:9][C@H:8]1[CH2:17][OH:18])=[O:6])[CH:2]=[CH2:3].[Cl-].[NH4+].[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([N:21]=[N+:22]=[N-:23])[CH2:9][C@H:8]1[CH2:17][OH:18])=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18639172(2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol

Product 1

HCID 57320993(2S,4S)-1-allyloxycarbonyl-4-azido-2-hydroxymethylpyrrolidine

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of (2S,4R)-1-allyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine (20.0 g) in N,N-dimethylformamide (200 ml) were added ammonium chloride (5.74 g) and sodium azide (6.98 g). The resulting mixture was heated at 75° C. for 8 hours. After cooling, the mixture was diluted with ethyl acetate (1 l) and aqueous sodium hydrogen carbonate (1 l). The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated in vacuo to give (2S,4S)-1-allyloxycarbonyl-4-azido-2-hydroxymethylpyrrolidine.

Workup

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-897b8bc684d34bdab13bb3900cec9b4d
Source dataset
uspto-grants-1992_01
Patent number
US05081237

Reaction notes

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