Acetyl chloride → HCID 11709540, compound

Participants

Reaction Steps

To a solution of (±)-trans-2-benzyl-6-methyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,4-c]isoquinoline from Example 105, Part A (28 mg, 0.1 mmol) in 1 mL of methylene chloride was added triethylamine (0.021 mL, 0.15 mmol) and acetyl chloride (0.009 mL, 0.15 mmol). The reaction was allowed to stir at ambient temperature for 2 h. The solution was concentrated and purified (ISCO, elution with 0-5% methanol/methylene chloride) to afford 25 mg of the title compound of Example 108 as an off-white solid. 1H NMR (CDCl3): δ 7.74-7.68 (m, 2H), 7.50-7.42 (m, 3H), 7.21-7.13 (m, 2H), 6.80-6.75 (m, 1H), 4.78 and 4.38 (ABq, 2H), 4.31-4.25 (m, 1H), 4.16-4.03 (m, 2H), 3.89-3.80 (m, 1H), 3.71-3.63 (m, 1H), 3.49 (s, 2H), 3.07-2.98 (m, 1H), 2.35 (s, 3H), 2.21 (s, 3H). LRMS (ESI): 321.3 (M+H)+.

Provenance & Evidence