Benzophenone → HCID 45275495、化合物

HRID 1667165ノート

反応式

HRID 1667165 の反応式
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8](=[O:29])[CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11]2=[O:28])[CH2:4][CH2:3]1.[C:30]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[BH4-].[Na+]>ClCCl.CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH:30]([NH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8](=[O:29])[CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:11]2=[O:28])[CH2:4][CH2:3]1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

参加物

7

反応物 3

HCID 3102BenzophenoneHCID 4311764Sodium borohydrideHCID 673590361-(2-(4-Aminopiperidin-1-yl)-2-oxoethyl)-3,3-diphenylpiperidin-2-one

生成物 1

HCID 45275495HCID 45275495、化合物

試薬・触媒・溶媒 3

HCID 11026Titanium isopropoxide触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 1-(2-(4-aminopiperidin-1-yl)-2-oxoethyl)-3,3-diphenylpiperidin-2-one (Example 87B, 0.1 g, 0.25 mmol) and benzophenone (0.056 g, 0.3 mmol) is stirred in dichloromethane (3 mL) with titanium(IV) isopropoxide (0.012 g, 0.4 mmol) for 3 hours. The reaction mixture was then diluted with methanol (10 mL) and sodium borohydride (0.4 g, 0.4 mmol) was added. The mixture was stirred at ambient temperature for 16 hours and then concentrated. The residue was partition in ethyl acetate/H2O (100 mL/20 mL). The organic layer was dried over MgSO4 and concentrated. The residue was chromatographed on silica gel eluting with 5-10% methanol/dichloromethane. 1H NMR (300 MHz, CDCl3) δ ppm 7.26-7.38 (m, 16H), 7.15-7.24 (m, 4H), 4.99 (s, 1H), 4.36-4.44 (m, 1H), 4.21 (s, 2H), 3.70-3.77 (m, 1H), 3.48 (t, J=6.4 Hz, 2H), 2.93-3.03 (m, 1H), 2.69-2.79 (m, 1H), 2.61-2.69 (m, 3H), 1.89-2.00 (m, 2H), 1.77-1.89 (m, 2H), 1.24-1.41 (m, 3H); MS (ESI+) m/z 558 (M+H)+.

後処理

  1. additionwas added
  2. concentrationconcentrated
  3. customThe residue was partition in ethyl acetate/H2O (100 mL/20 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel eluting with 5-10% methanol/dichloromethane

出典と根拠

ORDレコード
ord-5af95f79a713405784e4d45981b8d43f
出典データセット
uspto-grants-2011_10
特許番号
US08044069B2

反応ノート

読み込み中…