Phenylacetaldehyde → HCID 69055148, compound

Participants

Reaction Steps

To a solution of (±)-trans-2-benzyl-6-methyl-2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-one, from Example 101, Part A (57 mg, 0.2 mmol) in 10 mL of methanol was added phenylacetaldehyde (24 mg, 0.2 mmol) and 10% Pd/C catalyst (6 mg). The reaction mixture was purged several times with hydrogen and stirred under 1 atm of hydrogen, maintained by a balloon, for 18 h. The reaction mixture was filtered through a pad of Celite and concentrated in vacuo. The residue was purified (ISCO, elution with 0-8% methanol/methylene chloride) to afford the title compound of Example 102 as a solid. 1H NMR (CDCl3): δ 7.36-7.20 (m, 6H), 7.18 (d, 1H, J=7.7 Hz), 6.88 (d, 1H, J=7.7 Hz), 6.22 (broad s, 1H), 3.66-3.58 (m, 1H), 3.41 (app t, 1H, J=8.3 Hz), 3.30-3.22 (m, 1H), 3.14 (app t, 1H, J=7.7 Hz), 3.05-2.93 (m, 4H), 2.88-2.81 (m, 2H), 2.70 (s, 3H). LRMS (ESI): 307.3 (M+H)+.

Provenance & Evidence