Ethyl formate → HCID 86718468, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.5 g (2.2 mmol) S,S-Dimethyl-N-[(phenylmethoxy)-carbonyl]sulfoximine (J. Org. Chem., 2005, 70 (23), 9599) and THF is cooled to −78° C. and 2.3 ml (2.3 mmol) LiHMDS 1M in THF is added dropwise and the mixture is stirred for 20 minutes. 0.2 g (2.3 mmol) Ethyl formate in THF is added and the mixture is stirred at −78° C. for 50 minutes warmed to RT and stirred for additional 4 h. The Reaction mixture is diluted with water and EtOAc, the aqueous phase is separated and extracted with EtOAc. The organic phases are pooled and washed with water and brine, dried and evaporated. To a mixtue of the residual, 0.1 g (1.6 mmol) pyrrolidine and THF 0.1 g acetic acid and 0.4 g (2.0 mmol) NaBH(OAc)3 are added and the reaction mixture is stirred at RT over night. The reaction mixture is evaporated and purified by HPLC giving rise to benzyl N—[methyl-oxo-(2-pyrrolidin-1-ylethyl)-λ6-sulfanylidene]carbamate.

Provenance & Evidence