Cyclobutanone → 4-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-N-methyl-3-(methyloxy)benzamide

HRID 222752ノート

反応式

HRID 222752 の反応式
[CH3:1][NH:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:21]=[CH:20][C:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19][C:13]=3[CH:12]=2)=[C:6]([O:22][CH3:23])[CH:5]=1.[C:25]1(=O)[CH2:28][CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.CO>[CH:25]1([N:17]2[CH2:16][CH2:15][C:14]3[CH:20]=[CH:21][C:11]([O:10][C:7]4[CH:8]=[CH:9][C:4]([C:3]([NH:2][CH3:1])=[O:24])=[CH:5][C:6]=4[O:22][CH3:23])=[CH:12][C:13]=3[CH2:19][CH2:18]2)[CH2:28][CH2:27][CH2:26]1

参加物

7

反応物 3

HCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 57440300N-Methyl-3-(methyloxy)-4-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yloxy)benzamide

生成物 1

HCID 103176494-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-N-methyl-3-(methyloxy)benzamide収率 21.9%

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

N-Methyl-3-(methyloxy)-4-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yloxy)benzamide (E264, Step 6) (78 mg, 0.24 mmol) was dissolved in dry dichloromethane (5 ml), treated with cyclobutanone (0.04 ml, 0.48 mmol) and acetic acid (1 drop) and the resulting mixture stirred for 15 minutes. Sodium triacetoxyborohydride (102 mg, 0.48 mmol) was added and the mixture stirred for 30 minutes. The mixture was diluted with methanol and applied to a SCX column eluting with methanol and then a mixture of 0.880 ammonia/methanol (1:9). The basic fractions were combined and concentrated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of ammonia:methanol:dichloromethane (0.5:4.5:95 0.880) to afford the title compound (20 mg); MS (ES+) m/e 381 [M+H]+.

後処理

  1. stirringthe mixture stirred for 30 minutes
  2. washeluting with methanol
  3. additiona mixture of 0.880 ammonia/methanol (1:9)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography
  6. washeluting with a mixture of ammonia:methanol:dichloromethane (0.5:4.5:95 0.880)

出典と根拠

ORDレコード
ord-c30ec74fc13c4739b7555db3f93365a9
出典データセット
uspto-grants-2012_06
特許番号
US08207331B2

反応ノート

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