Triethylamine → Ammonium hydroxide methanol

HRID 270560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 270560
Cl.[NH2:2][C@@H:3]1[CH2:7][CH2:6][C@@:5]([C:11]([N:13]2[CH2:18][CH2:17][C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])([OH:19])[CH2:15][CH2:14]2)=[O:12])([CH:8]([CH3:10])[CH3:9])[CH2:4]1.[CH3:30][CH:31]1[C:36](=O)[CH2:35][CH2:34][O:33][CH2:32]1.C([N:40](CC)CC)C.[C:45](O[BH-](OC(=O)C)OC(=O)C)(=[O:47])C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH4+:2].[OH-:12].[NH4+:40].[OH-:33].[CH3:45][OH:47].[CH:8]([C@:5]1([C:11]([N:13]2[CH2:18][CH2:17][C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:27])[F:28])([OH:19])[CH2:15][CH2:14]2)=[O:12])[CH2:6][CH2:7][C@@H:3]([NH:2][CH:36]2[CH2:35][CH2:34][O:33][CH2:32][CH:31]2[CH3:30])[CH2:4]1)([CH3:10])[CH3:9]

Komponenten

9

Edukt 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 141709263-Methyloxan-4-oneHCID 689309271-{[(1S,3R)-3-amino-1-isopropylcyclopentyl]carbonyl}-4-[2-(trifluoromethyl)phenyl]piperidin-4-ol hydrochloride

Produkt 3

HCID 14923Ammonium HydroxideHCID 21894508Ammonium hydroxide methanolAusbeute 1 %HCID 68597077HCID 68597077, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-{[(1S,3R)-3-amino-1-isopropylcyclopentyl]carbonyl}-4-[2-(trifluoromethyl)phenyl]piperidin-4-ol hydrochloride (50 mg, 0.1 mmol), 3-methyltetrahydro-4H-pyran-4-one (39 mg, 0.34 mmol), and triethylamine (0.048 mL, 0.34 mmol) in methylene chloride (5 mL) was added sodium triacetoxyborohydride (73 mg, 0.34 mmol). After being stirred overnight at room temperature, a saturated solution of NaHCO3 was added. The solution was extracted with methylene chloride three times. The combined extracts were dried (MgSO4), filtered, and concentrated. Purification by flash chromatography on silica gel (0-20% B over 15 min. Bottle A=1% NH4OH/2% MeOH/EtOAc, Bottle B=1% NH4OH/MeOH) afforded the desired product as an oil. MS calculated for C27H39F3N2O3: (M+H) 497; found 497.2.

Aufarbeitung

  1. extractionThe solution was extracted with methylene chloride three times
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography on silica gel (0-20% B over 15 min

Quellen und Nachweise

ORD-Eintrag
ord-16e8affef9cc44f090a7f58699380b36
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449467B2

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