Sodium Bicarbonate → 5-[1-(2-Fluoro-2-methyl-propyl)-piperidin-4-ylmethoxy]-1'-methanesulfonyl-1',2',3',6'-tetrahydro-[2,4']bipyridinyl

HRID 222582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222582
[CH3:1][C:2](O)([CH3:28])[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][O:11][C:12]2[CH:13]=[N:14][C:15]([C:18]3[CH2:19][CH2:20][N:21]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:22][CH:23]=3)=[CH:16][CH:17]=2)[CH2:6][CH2:5]1.COCCN(S(F)(F)[F:40])CCOC.C(=O)(O)[O-].[Na+]>ClCCl>[F:40][C:2]([CH3:28])([CH3:1])[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH2:19][CH2:20][N:21]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:22][CH:23]=3)=[N:14][CH:13]=2)[CH2:6][CH2:5]1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 668647472-methyl-1-[4-[[6-(1-methylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)-3-pyridyl]oxymethyl]-1-piperidyl]propan-2-ol

Produkt 1

HCID 498434835-[1-(2-Fluoro-2-methyl-propyl)-piperidin-4-ylmethoxy]-1'-methanesulfonyl-1',2',3',6'-tetrahydro-[2,4']bipyridinylAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 2-methyl-1-[4-[[6-(1-methylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)-3-pyridyl]oxymethyl]-1-piperidyl]propan-2-ol (33 g; 77.91 mmoles) in dichloromethane (155 mL) is added bis(2-methoxyethyl)aminosulfur trifluoride (16.63 mL; 85.70 mmoles) at an internal temperature of 22-23° C. The reaction is stirred at 25° C. for 2 h. Aqueous saturated solution of sodium bicarbonate is added to pH 7. Layers are separated, the aqueous layer is extracted with dichloromethane (2×500 mL), the combined organic layers are dried over magnesium sulphate, filtered and concentrated. The crude material is purified by silica gel chromatography eluting with 98:2 dichloromethane:methanol. The solid is triturated with 500 mL of methyl t-butyl ether and filtered. The solid is dried in an oven at 40° C. for 3 days to obtain 24 g of the title compound as a white solid. MS (m/z) 426 (M+1).

Aufarbeitung

  1. customLayers are separated
  2. extractionthe aqueous layer is extracted with dichloromethane (2×500 mL)
  3. dry with materialthe combined organic layers are dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material is purified by silica gel chromatography
  7. washeluting with 98:2 dichloromethane
  8. customThe solid is triturated with 500 mL of methyl t-butyl ether
  9. filtrationfiltered
  10. customThe solid is dried in an oven at 40° C. for 3 days

Quellen und Nachweise

ORD-Eintrag
ord-8d2523a00d294a47aeffb418d6136561
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207344B2

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