反应详情

A mixture of (3R)-1-(2-methylamino-4-methoxy-phenyl)3,7-dimethyl-oct-6-en-1-ol (291 mg, 1 mmol), phenylboronic acid (365 mg, 3 mmol) and propionic acid (22 rag, 0.3 mmol) in benzene (10 mL) was refluxed for 20 h to give, after chromatography, 140 mg (51%) of (6aR,9 R, 10aR)-3-methoxy-5,6,6,9-tetramethyl-5,6,6a,7,8,9,10,10a-octahydro-phenanthridine: [α]D +37 (c 4.5, CHCl3); 1H nmr (400 MHz, CD3COCD3), δ 0.83 (q, 1H, J=11.6 Hz, H-10ax), 0.98 (d, 3H, J=6.5 Hz), 1.0 (s, 3H), 1.20 (m, 2H), 1.22 (m, 1H), 1.29 (s, 3H), 1.54 (m, 1H), 1.82 (m, 1H), 1.89 (m, 1H), 2.37 (dr, 1H, J=10.3, 2.7 Hz), 2.45 (m, 1H), 2.83 (s, 3H), 3.71 (s, 3H), 6.12 (d, 1H, J=2.4 Hz), 6.16 (dd, 1H, J=8.3, 2.4 Hz), 7.0 (d, 1H, J=8.3 Hz); 13C nmr (100.6 MHz, CD3COCD3), δ 19.1, 23.1, 26.5, 28.7, 32.4, 33.0, 35.8, 36.0, 41.3, 48.9, 55.1, 57.7, 99.2, 100.7, 120.2, 125.9, 147.8, 160.0. Exact Mass calcd. for C18H28NO (M+1): 274.2170; found: 274.2172.

1. temperaturewas refluxed for 20 h
2. customto give