反应详情

To a solution of methyl 1-((6-(tert-butyldimethylsilyloxy)naphthalen-2-yl)methyl)azetidine-3-carboxylate (4.5 g, 11.7 mmol) in methanol (50 mL) at 0° C. was added con. HCl (5 mL) dropwise. The reaction mixture was stirred at r.t for 1 h. The mixture was neutralized by sat. NaHCO3 and evaporated off most of solvent, extracted with DCM and washed with brine, dried over Na2SO4 and concentrated to obtain crude product. The crude product was purified by silica gel chromatography (DCM:MeOH=40:1), extracted with DCM and washed with brine, dried over Na2SO4 and concentrated to obtain crude product. The crude product was purified by silica gel chromatography (DCM:MeOH=40:1) to give the title compound (1.5 g, 47%) as a gray solid. ESI-MS (M+1)+: 272.0. 1H NMR (400 MHz, CDCl3) δ: 8.14 (s, 1H), 7.59-7.52 (m, 2H), 7.39-7.28 (m, 2H), 7.09-7.04 (m, 2H), 3.92 (s, 2H), 3.86-3.82 (m, 2H), 3.70 (s, 3H), 3.63-3.59 (m, 2H), 3.52-3.46 (m, 1H).

1. customevaporated off most of solvent
2. extractionextracted with DCM
3. washwashed with brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. customto obtain crude product
7. customThe crude product was purified by silica gel chromatography (DCM:MeOH=40:1)
8. extractionextracted with DCM
9. washwashed with brine
10. dry with materialdried over Na2SO4
11. concentrationconcentrated
12. customto obtain crude product
13. customThe crude product was purified by silica gel chromatography (DCM:MeOH=40:1)