Methanol → HCID 62005685, compound

HRID 450070Notes

Reaction equation

HRID 450070 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[C:15]([OH:17])=[O:16])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[CH3:22]O>>[CH3:22][O:16][C:15]([CH:11]1[CH2:12][CH2:13][CH2:14][N:10]1[C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 16769874HCID 16769874, compound

Product 1

HCID 62005685HCID 62005685, compoundYield 73%

Procedure

A solution of 1-(4-nitro-phenyl)-pyrrolidine-2-carboxylic acid (0.75 g, 3.17 mmol) in methanol (20 ml) was cooled to 0° C. Thionyl chloride (0.71 ml, 9.51 mmol) was added dropwise and then the reaction mixture was stirred at room temperature overnight. The reaction mixture was evaporated to dryness and then diluted with dichloromethane. The organic layer was washed with bicarbonate solution, water and dried. Evaporation to dryness yielded 1-(4-nitrophenyl)-pyrrolidine-2-carboxylic acid methyl ester (0.58 g, 73%).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additiondiluted with dichloromethane
  3. washThe organic layer was washed with bicarbonate solution, water
  4. customdried
  5. customEvaporation to dryness

Sources & evidence

ORD record
ord-d62ff746196e40088ad87e1122d5a9e9
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

Loading…