Tetrahydrofuran → HCID 18785874, compound

Participants

Reaction Steps

Tetra-n-butylammonium fluoride (1.0M in THF, 3.3 ml) was added to a stirred solution of 1-amino-3-(tert-butyldimethylsilyloxyphenyl)-3,4-dihydroisoquinoline hydrochloride (638 mg, 1.11 mmol) in THF (10 ml). After 15 min., the mixture was evaporated and the residue purified by flash chromatography on untreated neutral alumina, eluting with 5% methanol in dichloromethane, increasing the gradient to 40% methanol in dichloromethane to give a colourless solid (172 mg). This was recrystallised from methanol/dichloromethane (1:2) to give the product as a white powder. M+ 239; 360 MHz 1H n.m.r (d6 -DMSO) 9.65 (1H, br.s), 8.15 (1H, d, J 7.8 Hz), 7.69 (1H, t, J 7.5 Hz), 7.52 (1H, t, J 7.6 Hz), 7.45 (1H, d, J 7.5 Hz), 7.19 (2H, d, J 8.6 Hz), 6.77 (2H, d, J 8.6 Hz), 4.87 (1H, t, J 7.3 Hz), 3.25 (2H, d, J 7.3 Hz).

Provenance & Evidence