Sodium Azide → HCID 14555476, compound

HRID 2073174Notes

Reaction equation

HRID 2073174 reaction equation
CS(O[C@@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7]1)(=O)=O.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O>[N:21]([C@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7]1)=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 14555473(R)-1-((Benzyloxy)carbonyl)pyrrolidin-3-yl methanesulfonate

Product 1

HCID 14555476HCID 14555476, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 20.5 g (72 mmol) of (R)-3-[(methylsulfonyl)oxy]-1-pyrrolidinecarboxylic acid, phenylmethyl ester in 100 ml of dry N,N-dimethylformamide was treated with 6.5 g (0.1 mol) of sodium azide and heated at 90° for four hours. The solvent was removed in high vacuo at 50° and the residue was partitioned between ethyl acetate/water (250 ml each). The aqueous layer was reextracted with ethyl acetate and the combined organic fractions were washed with water, dried (MgSO4) and evaporated in vacuo to give 16.2 g of the title compound.

Workup

  1. temperatureheated at 90° for four hours
  2. customThe solvent was removed in high vacuo at 50°
  3. customthe residue was partitioned between ethyl acetate/water (250 ml each)
  4. washthe combined organic fractions were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-97bcf278752f427eb39077ab26afa329
Source dataset
uspto-grants-1990_04
Patent number
US04916141

Reaction notes

Loading…