Sodium Bicarbonate → 1,3-Diacetoxymethyl-5-[2-[1-[2-[4-(5-methylpyridin-2-ylamino)piperidin-1-yl]ethyl]cyclohexyl]ethoxy]benzene

HRID 2223921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2223921
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][C:15]2([CH2:21][CH:22]=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:9]=[C:8]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[CH:7]=1)(=[O:3])[CH3:2].[NH:29]1[CH2:34][CH2:33][CH:32]([NH:35][C:36]2[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][N:37]=2)[CH2:31][CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(O)(=O)C>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][C:15]2([CH2:21][CH2:22][N:29]3[CH2:34][CH2:33][CH:32]([NH:35][C:36]4[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][N:37]=4)[CH2:31][CH2:30]3)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:9]=[C:8]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[CH:7]=1)(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 230210485-Methyl-N-(piperidin-4-YL)pyridin-2-amineHCID 597148671,3-Diacetoxymethyl-5-[2-[1-(formylmethyl)cyclohexyl]ethoxy]benzene

Produkt 1

HCID 597149741,3-Diacetoxymethyl-5-[2-[1-[2-[4-(5-methylpyridin-2-ylamino)piperidin-1-yl]ethyl]cyclohexyl]ethoxy]benzeneAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

1,3-Diacetoxymethyl-5-[2-[1-(formylmethyl)cyclohexyl]ethoxy]benzene (synthesized in Example 32) (215 mg) and 2-(piperidin-4-ylamino)-5-methylpyridine (synthesized in Preparation Example 4-3) (126 mg) were dissolved in 1,2-dichloroethane (5 mL). To this was added acetic acid (0.04 mL) at room temperature. The solution was stirred for 45 minutes. Sodium triacetoxyborohydride (295 mg) was added to the solution at room temperature and it was stirred for 3 hours. Saturated aqueous sodium bicarbonate solution was added to the solution and it was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was then concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, chloroform-methanol (10:1)] to give the title compound (258 mg).

Aufarbeitung

  1. stirringit was stirred for 3 hours
  2. extractionwas extracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was then concentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography [silica gel, chloroform-methanol (10:1)]

Quellen und Nachweise

ORD-Eintrag
ord-4f23d2b4373d4053a194413b57b9d4e1
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07375115B2

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