Formaldehyde → tert-Butyl (3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrole-1(2H)-carboxylate

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To a solution of (3aR,6aR)-hexahydro-pyrrolo[3,4-b]pyrrole-1-carboxylic acid tert-butyl ester (18.31 g, 0.86 mol) in methanol (450 ml) was added paraformaldehyde (52 g, 1.72 mole) and the mixture was stirred at room temperature for 1 hour. Sodium cyanoborohydride was then added and the mixture was stirred at room temperature for 10 hours, diluted with 1N NaOH (450 ml), extracted with dichloromethane (5×200 ml). The combined organic layers were dried (Na2SO4), filtered and concentrated to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 4.18 (m, 1H) 3.47-3.59 (m, 1H) 3.34-3.46 (m, 2H) 2.75-2.90 (m, 1H) 2.71 (m, 1H) 2.44-2.60 (m, 2H) 2.29 (s, 3H) 1.89-2.06 (m, 1H) 1.65-1.81 (m, 1H) 1.42-1.49 (m, 9H). MS: (M+H)+=226.

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