Sodium Bicarbonate → 7-(6-Chloro-indole-1-sulfonyl)4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline

Participants

Reaction Steps

1-[7-(6-Chloro-indole-1-sulfonyl)-4,4-dimethyl-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone (D4) was N-deacetylated as described in Example 1 to afford, after treatment with sodium hydrogen carbonate solution, the title compound (E28). Treatment of a solution of this material in dichloromethane/diethyl ether with oxalic acid (1.5 equivalents) afforded the corresponding crystalline oxalate salt (65 mg, 42%), δH (CD3OD)/ppm 1.13 (6H, s), 2.71 (2H, br,s), 3.86 (2H, br,s), 6.61 (1H, d, J=3.7 Hz), 7.12 (1H, dd, J=8.4, 1.8 Hz), 7.40-7.86 (4H, m), 7.86 (1H, d, J=1.7 Hz). MS: m/z (MH30) 375/377.

Provenance & Evidence