N-boranyl-2-methylpropan-2-amine → 6-Bromo-2-(1-phenyl-ethyl)-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

Participants

Reaction Steps

t-Butylaminoborane (1080 mg, 12.42 mmol) was added to a suspension of AlCl3 (828 mg, 6.21 mmol) in 30 mL of dichloromethane at 0° C. and the reaction mixture was allowed to come to room temperature and stirred for 30 minutes. The product from step e) (746 mg, 2.07 mmol) dissolved in 10 mL dichloromethane was added to the borane/AlCl3 reaction mixture and stirred at room temperature for 12 hours. The reaction was quenched with 2 N NaOH to pH=12. The organic phase was separated washed with brine and dried with MgSO4. The solvent was evaporated leaving a white solid. The crude was purified by column chromatography (SiO2) using 5-50% ethylacetate-hexane gradient to afford the subtitle compound (536 mg, yield: 74.6%). MS calculated for C17H18BrNS+H: 348, observed: 348 and 350.

Provenance & Evidence