Formaldehyde → tert-Butyl 5-methylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Participants

Reaction Steps

Step BI (1): Sodium triacetoxyborohydride (666 mg, 3.14 mmol) was added to a magnetically stirred solution of tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (165 mg, 0.777 mmol) and 37% formaldehyde (144 mg, 1.77 mmol) in 1,2-dichloroethane (10 mL). The resulting mixture was allowed to stir at rt for 16 h. Sodium hydroxide solution (2 mL of a 1 N solution) was added with vigorous stirring. Stirring was stopped and the layers were allowed to separate. The organic layer was removed and concentrated in vacuo with heating. Acetone was added to the residue, and the solution was decanted. The decanted portion was concentrated in vacuo to afford 80 mg (46% yield) of tert-butyl 5-methylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate as a colorless oil.

Provenance & Evidence