Acetic Acid → 4-[3-(4-Hydroxy-4-phenyl-piperidin-1-yl)-propyl]-1-(3-trifluoromethyl-phenyl)-[1,4]diazepan-5-one

HRID 1096236Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096236
[O:1]=[C:2]1[N:8]([CH2:9][CH2:10][CH:11]=O)[CH2:7][CH2:6][N:5]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[CH2:4][CH2:3]1.[C:23]1([C:29]2([OH:35])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.B.N1C=CC=CC=1.CC(O)=O>ClCCCl.CCO>[OH:35][C:29]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:34][CH2:33][N:32]([CH2:11][CH2:10][CH2:9][N:8]2[C:2](=[O:1])[CH2:3][CH2:4][N:5]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[CH2:6][CH2:7]2)[CH2:31][CH2:30]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 963874-Phenylpiperidin-4-olHCID 2723995Borane;pyridineHCID 866383883-[7-Oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-propionaldehyde

Produkt 1

HCID 591592464-[3-(4-Hydroxy-4-phenyl-piperidin-1-yl)-propyl]-1-(3-trifluoromethyl-phenyl)-[1,4]diazepan-5-oneAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 229016121,2-Dichloroethane ethanolLösungsmittel

Versuchsvorschrift

To a solution of 3-[7-oxo-4-(3-trifluoromethyl-phenyl)-[1,4]diazepan-1-yl]-propionaldehyde 0.016 g (0.05 mmol) and 4-phenyl-piperidin-4-ol 0.018 g (0.10 mmol) in DCE/EtOH 1:1 (0.5 ml) was added pyridine-borane complex (25 μL of 8 M solution in pyridine, 0.2 mmol) and AcOH (25 μL, 0.4 mmol) and the mixture stirred for 16 h. The mixture was then evaporated to dryness and purified by preparative HPLC, affording the title compound 0.01 g (44%) as a white solid. MS: 476.2 (MH+).

Aufarbeitung

  1. customThe mixture was then evaporated to dryness
  2. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-08bf37eec1154abcab77aabfd51a5773
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138175B2

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