反应详情

A 1M borane solution in tetrahydrofuran (6 mL) was added to a solution of tert-butyl 4-(2-hydroxycarbonylphenyl)piperidinecarbamate (0.915 g) (prepared from 4-(2-methoxycarbonylphenyl)piperidine [Example 20] by N-protection using di-tert-butyldicarbonate followed by saponification of the methyl ester with lithium hydroxide) in tetrahydrofuran (20 mL) at 0° C. The reaction was warmed to ambient temperature and stirred overnight. The reaction was quenched with methanol and 1N aqueous HCl then extracted with diethyl ether. The organic phase was separated and extracted sequentially with aqueous sodium bicarbonate and brine. The organic phase was dried and evaporated to give the title compound (0.906 g) as a colorless oil. MS: m/z=192 (M-Boc). 1H NMR (CDCl3) δ 7.28 (m, 4H, Ar—H), 4.75 (d, 2H, Ar—CH2—O), 3.05 (m, 1H), 2.83 (m, 3H), 1.70 (m, 5H), 1.49 (s, 9H).

1. customat 0° C
2. customThe reaction was quenched with methanol and 1N aqueous HCl
3. extractionthen extracted with diethyl ether
4. customThe organic phase was separated
5. extractionextracted sequentially with aqueous sodium bicarbonate and brine
6. customThe organic phase was dried
7. customevaporated