Sulfuric acid magnesium salt (1:1) → {(2R,4S)-2-Benzyl-4-[(quinolin-4-ylmethyl)-amino]-piperidin-1-yl}-(3,5-bis-trifluoromethyl-phenyl)-methanone

HRID 1033329

Reaktionsgleichung

Reaktionsgleichung von HRID 1033329
[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH2:14])[CH2:11][CH2:10][N:9]1[C:15](=[O:30])[C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]([CH:41]=O)=[CH:33][CH:32]=1.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C1(C)C=CC=CC=1.CO>[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH:14][CH2:41][C:34]2[C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:31]=[CH:32][CH:33]=2)[CH2:11][CH2:10][N:9]1[C:15](=[O:30])[C:16]1[CH:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:19]=[C:18]([C:26]([F:29])([F:27])[F:28])[CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 780724-QuinolinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 22869971(2R,4S)-2-benzyl-1-(3,5-bis-(trifluoromethyl)benzoyl)-4-piperidinamine

Produkt 1

HCID 10370818{(2R,4S)-2-Benzyl-4-[(quinolin-4-ylmethyl)-amino]-piperidin-1-yl}-(3,5-bis-trifluoromethyl-phenyl)-methanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

3.35 g (7.78 mmol) of (2R,4S)-2-benzyl-1-(3,5-bis-(trifluoromethyl)benzoyl)-4-piperidinamine are reacted in analogy to Example 2 g with 1.34 g (8.56 mmol) of quinoline-4-carboxaldehyde and 1.3 g of magnesium sulfate in 30 ml of toluene, and subsequently reduced with 324 mg (8.56 mmol) of sodium borohydride in 25 ml of methanol. The title compound ##STR64## is obtained (3.5 g, 79%) as white foam. TLC: methylene chloride/methanol/conc. ammonia (1000:50:1) Rf =0.21, FD-MS: M+ =571, [α]D =+0.7 (c=1, MeOH), IR: 1635 cm-1.

Quellen und Nachweise

ORD-Eintrag
ord-54bddb55df9f419196bef92a9c83827e
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05310743

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