Aluminium lithium hydride → (2-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazol-6-yl)methanamine

Participants

Reaction Steps

To a stirred mixture of 2-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazole-6-carbonitrile (260 mg, 0.8 mmol) from Step 3 of this Example in THF (10 mL) at 0° C. was added LAH (3.3 mL of a 1M solution in THF, 3.3 mmol). The mixture was allowed to warm slowly to rt and stirred for 15 h. The mixture was again cooled to 0° C. and Na2SO4.10H2O was added slowly. The mixture was stirred for 2 h, filtered, and the filtrate was concentrated under reduced pressure to afford (2-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazol-6-yl)methanamine (237 mg). The material was used in the next step without further purification. LCMS (ESI) m/z 318 (M+H)+.

Provenance & Evidence