Acetone → HCID 11681450, compound

Participants

Reaction Steps

To a solution of (3aR,9bS)-6-chloro-8-ethyl-2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-one hydrochloride (Example 29) (19 mg, 0.066 mmol) in 2 mL of methanol was added acetone (0.015 mL, 0.20 mmol) followed by sodium borohydride (13 mg, 0.33 mmol) portionwise. The reaction mixture was stirred at ambient temperature for 18 h. The reaction was concentrated and the residue was purified (ISCO, elution with 0-15% methanol/methylene chloride) to afford the free base. To the free base in 1 mL of ether was added 4N HCl in dioxane (0.05 mL). The mixture was concentrated in vacuo, triturated with ether, and dried in vacuo to afford 13 mg (60%) of the title compound of Example 64 as a white solid. 1H NMR (CD3OD): 7.36 (s, 1H), 7.07 and 7.02 (s, 1H), 4.27-4.21 and 4.16-4.11 (m, 1H), 3.88-3.35 (overlapping m, 6H), 2.70 (q, 2H), 1.48-1.42 (m, 6H), 1.26 (t, 3H). LRMS (ESI): 293.3/295.3 (M+H)+.

Provenance & Evidence