Acetaldehyde → HCID 11580484, 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) (10 mg, 0.035 mmol) in 2 mL of methanol was added acetaldehyde (0.006 mL, 0.10 mmol) followed by sodium borohydride (7 mg, 0.17 mmol). 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 7 mg (64%) of the title compound of Example 65 as an off-white solid. 1H NMR (CD3OD): 7.27 (s, 1H), 6.95 and 6.91 (s, 1H), 4.30-4.25 and 3.93-3.85 (m, 2H), 3.70-52 (overlapping m, 3H), 3.42-3.27 (overlapping m, 3H), 2.61 (q, 2H), 1.33 (q, 3H), 1.16 (t, 3H). LRMS (ESI): 279.2/281.2 (M+H)+.

Provenance & Evidence