Dimethyl Sulfide → Ammonia methanol

Participants

Reaction Conditions

Reaction Steps

(+/−)-cis-tert-Butyl-5-benzyl-3a-fluoro-4,6-dioxohexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (160 mg, 0.459 mmol) was dissolved in THF (4.5 mL), and BH3.Me2S (0.174 mL, 1.84 mmol, 4.00 eq) was added at ambient temperature. The reaction mixture was stirred at 55° C. for 1.5 hr. A light slurry was formed during the reaction. The reaction was then cooled to 0° C. and quenched with dry MeOH (2 mL) dropwise followed by concentrated HCl until pH=4. The reaction solution was stirred at 0-10° C. for 1 hr. The temperature was raised to 55° C. for 1.5 hr was then cooled to rt and stirred for 20 hr. The reaction mixture was concentrated under reduced pressure, diluted with MeOH, neutralized by passing through an SCX column with MeOH and then 7 N NH3/MeOH and obtained the free amine. The title product was carried forward without further purification (100 mg, crude) m/z (APCI+) for C13H17FN2 221.25 (M+H)+.

Provenance & Evidence