Water → 1'-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,5-triazin-2-yl]-1,4'-bipiperidinyl-3-ol

HRID 2175088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2175088
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[N:13]=[CH:12][N:11]=[C:10]([N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[CH2:25][CH2:24][CH2:23][CH:22]([OH:26])[CH2:21]3)[CH2:16][CH2:15]2)[N:9]=1.CC1(C)C(C)(C)OB([C:35]2[CH:44]=[CH:43][C:42]3[C:41]([CH3:46])([CH3:45])[CH2:40][CH2:39][C:38]([CH3:48])([CH3:47])[C:37]=3[CH:36]=2)O1.O>C1(C)C=CC=CC=1.C(O)C.O>[CH3:45][C:41]1([CH3:46])[CH2:40][CH2:39][C:38]([CH3:48])([CH3:47])[C:37]2[CH:36]=[C:35]([C:8]3[N:13]=[CH:12][N:11]=[C:10]([N:14]4[CH2:19][CH2:18][CH:17]([N:20]5[CH2:25][CH2:24][CH2:23][CH:22]([OH:26])[CH2:21]5)[CH2:16][CH2:15]4)[N:9]=3)[CH:44]=[CH:43][C:42]1=2

Komponenten

6

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 112439294,4,5,5-Tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolaneHCID 532524851-[1-(4-Chloro-1,3,5-triazin-2-yl)piperidin-4-yl]piperidin-3-ol

Produkt 1

HCID 532504051'-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,5-triazin-2-yl]-1,4'-bipiperidinyl-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86587398Ethanol toluene waterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

45 mg (0.42 mmol) of sodium carbonate are added to 50 mg (0.17 mmol) of 1′-(4-chloro-1,3,5-triazin-2-yl)-1,4′-bipiperidinyl-3-ol and 139 mg (0.42 mmol) of 4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane in 3.2 ml of toluene/ethanol/water (3.2/3.2/1). The reaction mixture is degassed a number of times, and 19 mg (0.017 mmol) of tetrakis-(triphenylphosphine)palladium(0) are added under nitrogen atmosphere, the mixture is treated in an ultrasound bath for 10 min and subsequently heated at 90° C. for 5 h. Water is added to the reaction mixture, which is then extracted three times with ethyl acetate/ether. The combined organic phases are dried over Na2SO4 and evaporated. The crude product is purified by means of preparative HPLC.

Aufarbeitung

  1. additionare added under nitrogen atmosphere
  2. additionthe mixture is treated in an ultrasound bath for 10 min
  3. extractionis then extracted three times with ethyl acetate/ether
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated
  6. customThe crude product is purified by means of preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-13578d4c243e4abc8f1e0d5c41f7dbd9
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062015B2

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