반응 #73455
ord-ccd1a503b4e54b72a9bf1f0908587715
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시약
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후처리
- 1세척washed with water (2×40 mL)
- 2기타dried
- 3기타Evaporation of organic layer
- 4기타gave a residue
- 5기타The residue was triturated with diisopropyl ether (20 mL)
실험 절차
To a solution of compound 10 (3.00 g, 11.6 mmol) in CH2Cl2 at 0° C. (60 mL) was added piperazine-1-ethanol (11) (1.82 g, 14.0 mmol), EDC (3.12 g, 16.3 mmol), HOBt (0.20 g) and DIPEA (5.8 mL, 34.9 mmol). The mixture was allowed to warm to RT over 16 h. TLC (5% MeOH/CH2Cl2) showed no starting material. The reaction mixture was diluted with CH2Cl2 (50 mL), washed with water (2×40 mL) and dried. Evaporation of organic layer gave a residue. The residue was triturated with diisopropyl ether (20 mL) to get 3-[4-(2-hydroxy-ethyl)-piperazine-1-carbonyl]-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester (12) as a white solid. Yield: 3.24 g (72%). Mp 72-75 C. 1H NMR (300 MHz, CDCl3) δ 1.42-1.56 (m, 2H); 1.76-1.82 (m, 2H); 2.02 (s, 2H); 2.29-2.51 (m, 4H); 2.90 (d, J=6.4 Hz, 1H); 3.08 (d, J=6.1 Hz, 1H); 3.18-3.24 (m, 2H); 3.41 (bs, 1H); 3.60 (t, J=2.3 Hz, 2H); 3.69 (bs, 1H); 4.90 (dd, J=6.8 Hz, 2.3 Hz, 2H); 5.08 (s, 2H); 7.28-7.40 (m, 5H).