Pyrrolidone carboxylic acid → 5-(((Methylsulfonyl)oxy)methyl)-2-pyrrolidinone

An ice cold solution of 5-(hydroxymethyl)pyrrolidin-2-one (1.5 g, 13 mmol) prepared from 2-pyrrolidone-5-carboxylic acid (Valesinas et al., J. Org. Chem. 1992, 57, 2156-2160) in 20 mL of dichloromethane was treated with triethylamine (2.4 g, 23.5 mmol) and methylsulfonyl chloride (2.2 g, 19 mmol). The resulting solution was stirred at room temperature for 18 h. The reaction mixture was filtered to remove triethylamine hydrochloride and the filtrate was evaporated under reduced pressure. The crude, oily material was purified by chromatography (silica gel; 10% methanol in chloroform) to give 2.1 g of 5-(methanesulfonyloxymethyl)pyrrolidin-2-one as an oil which solidified upon addition of ether.

1. filtrationThe reaction mixture was filtered
2. customto remove triethylamine hydrochloride
3. customthe filtrate was evaporated under reduced pressure
4. customThe crude, oily material was purified by chromatography (silica gel; 10% methanol in chloroform)

ORD record

ord-d29ee879b4af4e7a85f1718d928580ec

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06509359B1