反应详情

Alkylation of (R)-alcohol 159 with 4-bromobenzyl bromide (1.3 equiv.) and NaH (1.5 equiv.) as in Example 2UU above for 3 h, followed by chromatography of the product on silica gel, eluting with CH2Cl2 (foreruns) and then with 1% EtOAc/CH2Cl2, gave (7R)-7-{[(4-bromobenzyl)oxy]methyl}-7-methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (160) (349 mg, 57%) as a white solid: mp (CH2Cl2/hexane) 157-159° C.; 1H NMR (CDCl3) δ 7.46 (dt, J=8.3, 2.0 Hz, 2H), 7.39 (s, 1H), 7.12 (br d, J=8.3 Hz, 2H), 4.50 (s, 2H), 4.09 (ddd, J=12.5, 6.9, 6.0 Hz, 1H), 4.01 (ddd, J=12.5, 7.0, 6.0 Hz, 1H), 3.62 (d, J=10.2 Hz, 1H), 3.58 (d, J=10.2 Hz, 1H), 2.37 (ddd, J=14.4, 7.0, 6.0 Hz, 1H), 2.10 (ddd, J=14.4, 6.9, 6.1 Hz, 1H), 1.46 (s, 3H); [α]D27 30.0° (c 1.00, CHCl3); HRFABMS calcd for C15H17BrN3O4 m/z [M+H]+ 384.0382, 382.0402. found 384.0385, 382.0398.

1. customabove for 3 h
2. washeluting with CH2Cl2 (foreruns)