Benzophenone → HCID 45275495, 화합물

HRID 1667165노트

반응식

HRID 1667165 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 45275495HCID 45275495, 화합물

시약·촉매·용매 3

HCID 11026Titanium isopropoxide촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-5af95f79a713405784e4d45981b8d43f
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044069B2

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