Dimethyl Sulfoxide → HCID 86643541, compound

Participants

Reaction Steps

To a cold (−60° C.) solution of oxalyl chloride (0.14 mL, 1.2 eq) in dry DCM (3.7 mL) was added dropwise a solution of DMSO (0.215 mL, 2.2 eq) in dry DCM (2.9 mL) within 4 min. After 10 min, was added dropwise (1S,2S,5R)-2-hydroxymethyl-3-aza-bicyclo[3.3.0]-octane-3-carboxylic acid tert.-butyl ester (330 mg) in dry DCM (1.7 mL) during 5 min. After 2 min a white suspension was formed. Stirring was continued 30 min at −55° C., then DIPEA (1.17 mL, 5 eq) (which was dried over 3A M.S.) was added during 3-4 min. The reaction mixture was allowed to come to RT, diluted with water and extracted with DCM. The combined org. extracts were washed with citric acid (5%), brine, dried over anh. MgSO4, filtered and evaporated to yield the title compound as an oil which was used for the next step without further purification.

Provenance & Evidence