Benzophenone → HCID 45275495, Verbindung

HRID 1667165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667165
[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

Komponenten

7

Edukt 3

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

Produkt 1

HCID 45275495HCID 45275495, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11026Titanium isopropoxideKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5af95f79a713405784e4d45981b8d43f
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044069B2

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