Potassium tert-butoxide → HCID 90308599, compound

Participants

Reaction Steps

A solution of tert-butyl-N-((4aS,11bR)-10-nitro-3,3,11b-trimethyl-4,4-dioxido-3,4a,5,6,7,11b-hexahydrobenzo[3,4]cyclohepta[1,2-b][1,4]thiazin-2-yl)-N-tert-butoxycarbonyl-carbamate (806 mg, 1.461 mmol) in THF (10 ml) was treated with potassium tert-butoxide (1M in THF) (0.584 ml, 0.584 mmol) dropwise at rt. The mixture became dark after first few drops added. After 5 min stirring the reaction was quenched by 3 ml sat NH4Cl solution, stirred for 5 min, then diluted with water (2 ml) and EtOAc (3 ml). Organic layer was washed with brine and concentrated. The residue was purified by FC using 40 g RediSep Gold column (10-70% EtOAc in heptane) to afford tert-butyl-N-((4aR,11bR)-10-nitro-3,3,11b-trimethyl-4,4-dioxido-3,4a,5,6,7,11b-hexahydrobenzo[3,4]cyclohepta[1,2-b][1,4]thiazin-2-yl)-N-tertbutoxycarbonyl-carbamate (615 mg, 1.115 mmol, 76% yield). LC/MS (ESI+) m/z=574 (M+Na).

Provenance & Evidence