Pyridine → HCID 69429519, compound

HRID 1006850Notes

Reaction equation

HRID 1006850 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2].N1C=CC=CC=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH2:14]([O:13][C:11]([CH:10]1[CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][N:8]([S:23]([CH3:22])(=[O:25])=[O:24])[CH2:9]1)=[O:12])[CH3:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 10954939HCID 10954939, compound

Product 1

HCID 69429519HCID 69429519, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3RS,4RS)-pyrrolidine-3,4-dicarboxylic acid diethyl ester (2.04 g, 9.48 mmol) [Bull. Soc. Chim. Fr. 1988, 579] in dichloromethane (30 ml) was added pyridine (1.12 g, 14.22 mmol), N,N-dimethylaminopyridine (10 mg) and methanesulfonyl chloride (1.30 g, 11.38 mmol) and stirred for 2 h at RT The solution was washed with 0.5 M aqueous HCl and water, dried and evaporated. Flash chromatography (EtOAc/hexane 1:1) gave 1.6 g (42%) of (3RS,4RS)-1-methanesulfonyl-pyrrolidine-3,4-dicarboxylic acid diethyl ester as a colorless solid, MS: 310 (M+NH4)+.

Workup

  1. washwas washed with 0.5 M aqueous HCl and water
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-47371e8027cc44c6adb008ea54c57704
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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