(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid → (2S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid

Participants

Reaction Steps

Jones' reagent (3.9 mL, 31.3 mmol) is added dropwise over a period of 5 mins to a solution of Boc-L-hydroxyproline (1 g, 4.3 mmol) in acetone (55 mL). The stirring is continued for an additional 30 minutes. The reaction is quenched with methanol (1 mL) and stirred at room temperature for 10 minutes. The reaction mixture is filtered through Celite® and the filtrate is concentrated under reduced pressure. It was diluted with water and extracted with dichloromethane 3 times. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield the title compound. ESI m/z 130 [M+H+−100].

Provenance & Evidence