反応式
[NH:1]1[CH2:4][CH:3]([CH:5]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)[C:6]([O:8][CH3:9])=[O:7])[CH2:2]1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=O)[CH2:26]CCC)=[CH:21][CH:20]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([N:1]2[CH2:4][CH:3]([CH:5]([C:10]3[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=3)[C:6]([O:8][CH3:9])=[O:7])[CH2:2]2)[CH3:26])=[CH:21][CH:20]=1参加物
実験手順
A solution of 0.015 g (0.054 mmole) of methyl azetidin-3-yl(3,5-difluorophenyl)acetate, 0.020 g (0.101 mmol) of 1-(4-chlorophenyl)pentan-1-one and 0.015 mL (0.12 mmol) of triethylamine in 5 mL of dichloroethane was stirred at room temperature. After 5 min, 0.050 g (0.237 mmol) of sodium triacetoxyborohydride was added and the mixture was stirred at room temperature for 6 h. The reaction was quenched by addition of saturated K2CO3 solution and the mixture was partitioned between 10 mL ether and 2 mL saturated K2CO3 solution. The layers were separated and the organic layer was dried over Na2SO4, and concentrated. The residue was purified by reverse phase chromatography (Waters Xterra C18, 19 mm×10 mm) using a gradient of CH3CN—H2O-Et3N (20:80:0.1 to 60:40:0.1). Homogenous fractions were pooled and concentrated to afford the title compound as a mixture of isomers; Mass Spectrum: m/e=422 (M+1 35Cl and 424 (M+1 37Cl). Mass Spectrum: m/e=422 (M+1 35Cl and 424 (M+1 37Cl).
後処理
- customThe reaction was quenched by addition of saturated K2CO3 solution
- customthe mixture was partitioned between 10 mL ether and 2 mL saturated K2CO3 solution
- customThe layers were separated
- dry with materialthe organic layer was dried over Na2SO4
- concentrationconcentrated
- customThe residue was purified by reverse phase chromatography (Waters Xterra C18, 19 mm×10 mm)
- concentrationconcentrated
出典と根拠
- ORDレコード
- ord-8a04fb2f3333474f9374b64141d63907
- 出典データセット
- uspto-grants-2011_03
- 特許番号
- US07906503B2
関連ノート
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