Hydrochloric Acid → HCID 131727574, compound

Participants

Reaction Steps

To a solution of (±)-trans tert-butyl 8-ethyl-6-methyl-5-oxo-4-(2-(pyridin-3-yloxy)ethyl)-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate (20 mg, 0.044 mmol) in 4 mL of ether was added 1 mL of 12 N HCl. The reaction was stirred vigorously for 5 min and then was diluted with 5 mL of water. The reaction was washed with ethyl acetate twice to remove the triphenylphosphine impurity. The aqueous layer was concentrated in vacuo, taken up in water, filtered and lyophilized to afford 8 mg (44%) of the title compound of Example 89 as a light tan powder. 1H NMR (DMSO-D6): δ 9.96-9.90 (broad m, 3H), 8.71 (s, 1H), 8.31-8.26 (m, 1H), 8.03-7.98 (m, 1H), 7.69-7.63 (m, 1H), 6.99 (s, 1H), 6.83 (s, 1H), 4.28-4.23 (m, 1H), 4.20-4.15 (m, 1H), 4.07-4.00 (m, 1H), 3.90-3.84 3.82-3.70 (overlapping m, 2H), 3.55-3.49 (m, 1H), 3.46-3.39 (m, 1H), 3.33-3.26 (m, 1H), 3.21-3.14 (m, 1H), 2.50 (q, 2H, J=7.5 Hz), 2.46 (s, 3H), 1.08 (t, 3H, J=7.7 Hz). LRMS (ESI): 352.1 (M+H)+.

Provenance & Evidence