Methanesulfonyl chloride → (R)-1-((Benzyloxy)carbonyl)pyrrolidin-3-yl methanesulfonate

HRID 232042Notes

Reaction equation

HRID 232042 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>N1C=CC=CC=1>[CH3:17][S:18]([O:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1)(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 11183628(R)-(-)-1-CBZ-3-pyrrolidinol

Product 1

HCID 14555473(R)-1-((Benzyloxy)carbonyl)pyrrolidin-3-yl methanesulfonateYield 84.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 17.5 g (84 mmol) of (R)-3-hydroxy-1-pyrrolidinecarboxylic acid, phenylmethyl ester in 150 ml of dry pyridine was cooled to 5° and treated dropwise with 11.5 g (0.1 mol) of methanesulfonyl chloride keeping the temperature at 5°. The reaction mixture was stirred at 5° for two hours and stored at 5° for 18 hours. The reaction mixture was allowed to warm to room temperature over three hours and the solvent was then removed in vacuo. The residue was partitioned between ethyl acetate/water (500 ml each) and the aqueous layer was reextracted with ethyl acetate. The combined organic layers were washed with water, dried (MgSO4) and evaporated in vacuo to give 21.2 g of the title compound.

Workup

  1. waitstored at 5° for 18 hours
  2. customthe solvent was then removed in vacuo
  3. customThe residue was partitioned between ethyl acetate/water (500 ml each)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-691eca76e4e54f2692fe74fe81397318
Source dataset
uspto-grants-1989_07
Patent number
US04851418

Reaction notes

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