Trifluoroacetic acid → (R)-5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-piperidin-4-yl-2,3-dihydro-furo[2,3-c]pyridine

HRID 872200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872200
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([C@@H:21]2[O:39][C:24]3=[CH:25][N:26]=[C:27]([C:29]4[CH2:30][CH2:31][N:32]([S:35]([CH3:38])(=[O:37])=[O:36])[CH2:33][CH:34]=4)[CH:28]=[C:23]3[CH2:22]2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl.[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>[CH3:38][S:35]([N:32]1[CH2:31][CH:30]=[C:29]([C:27]2[CH:28]=[C:23]3[CH2:22][C@H:21]([CH:18]4[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]4)[O:39][C:24]3=[CH:25][N:26]=2)[CH2:34][CH2:33]1)(=[O:36])=[O:37]

Komponenten

6

Edukt 2

HCID 6422Trifluoroacetic acidHCID 71208290HCID 71208290, Verbindung

Produkt 1

HCID 71208337(R)-5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-piperidin-4-yl-2,3-dihydro-furo[2,3-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittel2×HCID 10340Sodium CarbonateLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (2 mL) is added to a solution of (R)-4-[5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2,3-dihydro-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (1.0 g) in dichloromethane (10 mL) at room temperature. The solution is stirred at room temperature overnight and then diluted with dichloromethane, 2 N aqueous NaOH solution, and saturated aqueous Na2CO3 solution. The resulting mixture is vigorously stirred for 20 min and then extracted with dichloromethane. The combined extract is dried (Na2SO4) and concentrated to give the title compound. Mass spectrum (ESI+): m/z=364 [M+H]+.

Aufarbeitung

  1. stirringThe resulting mixture is vigorously stirred for 20 min
  2. extractionextracted with dichloromethane
  3. extractionThe combined extract
  4. dry with materialis dried (Na2SO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8a155cdebad54860ba055472dd3ebcb6
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975277B2

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