反应详情

温度

0 °C

A solution of (S)—N1—((S)-1-(4-bromophenyl)ethyl)-6-methyl-4-phenylhept-6-ene-1,4-diamine HCl salt (0.88 g, 2.2 mmol) in CH2Cl2 (120 mL) was cooled to 0° C. and i-Pr2NEt (1.15 mL, 3 equiv) was added. A solution of triphosgene (215 mg, 0.33 equiv) in CH2Cl2 (15 mL) was added dropwise over 10 min The mixture was stirred for 3 h at 0° C. LC-MS found the reaction completed. The mixture was concentrated, redissolved in 6:1 Ether/EtOAc (70 mL), washed with 1% aq HCl (2×15 mL), satd aq NaHCO3 (10 mL) and brine (10 mL), and dried over over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a 40-g silica gel cartridge, eluted with a 5˜40% EtOAc in Hexanes gradient, to afford (S)-1-((S)-1-(4-bromophenyl)ethyl)-4-(2-methylallyl)-4-phenyl-1,3-diazepan-2-one (487 mg, 52%) as a clear oil. LC-MS Method 1 tR=2.25 min, m/z 427, 429 (M+1); 1H NMR (CDCl3) δ 7.42 (d, 2H), 7.35 (t, 2H), 7.28-7.20 (m, 3H), 6.76 (d, 2H), 5.37 (q, 1H), 5.21 (s, 1h), 4.98 (s, 1H), 4.85 (s, 1H), 2.78 (m, 2H), 2.44 (m, 3H), 1.89 (td, 1H), 1.43 (d, 3H), 1.24 (m, 1H), 1.11 (s, 3H).

1. concentrationThe mixture was concentrated
2. dissolutionredissolved in 6:1 Ether/EtOAc (70 mL)
3. washwashed with 1% aq HCl (2×15 mL)
4. dry with materialdried over over Na2SO4
5. filtrationAfter filtration and concentration
6. customthe residue was purified by chromatography on a 40-g silica gel cartridge
7. washeluted with a 5˜40% EtOAc in Hexanes gradient