Triethylamine → (2S,4R)-tert-butyl-4-(tert-butyldimethylsilyloxy)-2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

To a solution of N-t-butoxycarbonyl-4(R)-t-butyldimethylsilyloxy-2(S)-hydroxymethylpyrrolidine (50.0 g, 150.8 mmol) and triethylamine (42.0 ml, 300 mmol) in CH2Cl2 (11) was added methane sulfonyl chloride (12.4 ml, 160 mmol) over a period of 5 minutes and stirring was continued for 1 hour. The solvent was evaporated in vacuo diluted with EtOAc (800 mL) and washed sequentially with aqueous citric acid and NaHCO3. The organic extracts were dried (Na2SO4), evaporated in vacuo and the residue purified by chromatography (SiO2, 15% EtOAc in hexanes). The title compound was obtained as a pale yellow solid FAB Mass spectrum, m/z=410(M+1).

Provenance & Evidence