反応式
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([CH:15]=O)[CH2:11][O:12]2)=[CH:7][CH:6]=1.[NH:17]1[CH2:22][CH2:21][CH2:20][C@@H:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([CH2:15][N:17]3[CH2:22][CH2:21][CH2:20][C@@H:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:18]3)[CH2:11][O:12]2)=[CH:7][CH:6]=1参加物
6
反応物 4
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 80 °C
実験手順
To a solution of 7-(methoxymethoxy)-2H-chromene-3-carbaldehyde (5.00 g) and ethyl (3R)-piperidine-3-carboxylate (4.20 mL) in dichloroethane (150 mL) was added sodium triacetoxyborohydride (12.0 g), followed by stirring at 80° C. for 4 hours. The reaction liquid was cooled to room temperature and then saturated aqueous NaHCO3 was added thereto, followed by extraction with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the vehicle was evaporated. The residue was purified by silica gel column chromatography (hexane:EtOAc=4:1) to obtain ethyl (3R)-1-{[7-(methoxymethoxy)-2H-chromen-3-yl]methyl}piperidine-3-carboxylate (7.30 g) as a yellow oily substance.
後処理
- customThe reaction liquid
- temperaturewas cooled to room temperature
- extractionfollowed by extraction with chloroform
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- customthe vehicle was evaporated
- customThe residue was purified by silica gel column chromatography (hexane:EtOAc=4:1)
出典と根拠
- ORDレコード
- ord-5af4ddab628246b4be6b910b01411837
- 出典データセット
- uspto-grants-2012_06
- 特許番号
- US08193378B2
関連ノート
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