Acetic Acid → HCID 59511942, compound

Participants

Reaction Steps

To a solution of 5-(1,3-benzodioxol-5-yl)-3,3-dimethyl-3,4-dihydro-2H-pyrrole (363 mg, 1.673 mmol) in acetonitrile (35 mL) add sodium triacetoxyborohydride (390 mg, 1.84 mmol) and stir at room temperature for two days. Then add more sodium triaxetoxyborohydride (390 mg, 1.84 mmol) and acetic acid and stir for 3 h. Add more add sodium triaxetoxyborohydride (390 mg, 1.84 mmol). After 0.5 h dissolve the reaction by adding methanol and load onto an ion-exchange SCX-2 (25 g), wash with methanol and then extract with ammonia in methanol. Concentrate under reduced pressure the basic solution, to afford 289 mg (79%) of the title compound. MS: 220 [M+H]+; 1H NMR (300 MHz, CDCl3): δ 6.90 (s, 1H), 6.72-6.75 (m, 1H), 6.72-6.75 (m, 1H), 5.91 (s, 2H), 4.20-4.25 (m, 1H), 2.68-2.72 (m, 1H), 2.75-2.79 (m, 1H), 1.72-1.98 (m, 2H), 1.45-1.1.53 (m, 1H), 1.10-1.18 (m, 6H).

Provenance & Evidence