Trifluoroacetic acid → HCID 11091606, compound

Participants

Reaction Steps

3-[1-(2S-Amino-3-methylbutyl)-3R,4R-dimethyl-4-piperidinyl]phenol (23) was coupled to 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid as described for compound 15 and de-protected with TFA as previously described to give crude product which was purified by silica preparative thin layer chromatography (50% (CHCl3:MeOH:NH4OH, 80:18:2) in CHCl3, yielding 0.028 g (3R)-N-((1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (16). 1H NMR (CDCl3): 7.22 (d, J=8.8 Hz, 1H), 7.05-7.13 (m, 3H), 6.98-7.01 (m, 1H), 6.79 (s, 1H), 6.73 (d, J=7.8 Hz, 1H), 6.65 (dd, J=7.9, 1.8 Hz, 1H), 4.05-4.14 (m, 1H), 3.99 (s, 2H), 3.56 (dd, J=10.7, 4.9 Hz, 1H), 3.18 (dd, J=16.5,4.8 Hz, 1H), 2.67-2.82 (m, 3H), 2.31-2.54 (m, 4H), 2.18-2.25 (m, 1H), 1.86-1.96 (m, 2H), 1.52 (d, J=12.9 Hz, 1H), 1.25 (s, 3H), 0.92 (t, J=7.6 Hz, 6H), 0.67 (d, J=6.9 Hz, 3H). LRMS (ES) m/z 450.3.2 (M+H)+.

Provenance & Evidence