Water → HCID 11230046、化合物

反応式

[H-].[Na+].[NH:3]1[C:9](=[O:10])[CH2:8][CH2:7][CH2:6][C:5]2[CH:11]=[CH:12][CH:13]=[CH:14][C:4]1=2.[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1.O.[CH3:26][N:27]([CH:29]=[O:30])C>>[OH:16][NH:3][C:9](=[O:10])[CH2:8][CH:7]1[C:29](=[O:30])[NH:27][C:26]2[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=2[CH2:5][CH2:6]1.[CH2:15]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:3]2[C:9](=[O:10])[CH2:8][CH2:7][CH2:6][C:5]3[CH:11]=[CH:12][CH:13]=[CH:14][C:4]2=3)=[CH:19][CH:18]=1)[CH3:26]

参加物

反応物 5

HCID 962Water

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 699934-Methyloxybenzyl chloride

HCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

生成物 2

HCID 11230046HCID 11230046、化合物

HCID 69009900HCID 69009900、化合物

反応条件

温度: 0 °C

実験手順

NaH (60% in mineral oil) (1.86 mmol) is added to a solution a 1,3,4,5-tetrahydro-benzo[b]azepin-2-one (1.55 mmol) in 5 mL of DMF at 0° C., After stirring at 0° C. for 15 minutes, the mixture is allowed to warm up to room temperature. p-Methoxybenzyl chloride (1.94 mmol) is added to the mixture. After stirring at room temperature for 16 hours, the mixture is poured into 50 mL of water and extracted with EtOAc (3×25 mL). The organic layer are combined, washed with brine and dried over MgSO4. After removing the solvent under reduced pressure, the residue is purified by flash column chromatography (silica gel) to provide the desired product 1-(4-ethoxy-benzyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one as white solid. Yield: 90%. MS: (ES+): 282.1 [M+1].

後処理

temperatureto warm up to room temperature
stirringAfter stirring at room temperature for 16 hours
extractionextracted with EtOAc (3×25 mL)
washwashed with brine
dry with materialdried over MgSO4
customAfter removing the solvent under reduced pressure
customthe residue is purified by flash column chromatography (silica gel)

出典と根拠

ORDレコード: ord-b0d09d4424934fc08b9c66d42bda7424
出典データセット: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07579363B2

反応ノート

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