Hydrochloric Acid → HCID 20505488, compound

Participants

Reaction Steps

To a solution of dimethylamine (18.5 ml of a 2N solution in methanol, 36.9 mmoles) in methanol (80 ml) was added a solution of hydrochloric acid in methanol (2.5 ml of a 5N solution in methanol) followed by trans 1-(t-butyldimethylsilyl)-3-formyl-4-tritylthio-2-azetidinone (3.0 g, 6.16 mmoles) and by sodium cyanoborohydride (0.27 g, 4.31 mmoles). The mixture was stirred at room temperature for 3.5 h, poured onto ice-hydrochloric acid (pH=2) and made basic with sodium hydroxide (1N NaOH, pH=9). The mixture was extracted with ether and the ether phase was washed with brine, dried and evaporated to give the title compound as a crude oil (3.0 g).

Provenance & Evidence