Lithium Hydroxide → (R)-4-(4-((tert-Butyldimethylsilyloxy)(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)benzoic acid

HRID 1476266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1476266
[OH-].[Li+].[Si:3]([O:10][C@@H:11]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=1)[CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:28]=[CH:27][C:21]([C:22]([O:24]CC)=[O:23])=[CH:20][CH:19]=2)[CH2:14][CH2:13]1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]>C1COCC1.CO.O>[Si:3]([O:10][C@@H:11]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=1)[CH:12]1[CH2:13][CH2:14][N:15]([C:18]2[CH:28]=[CH:27][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)[CH2:16][CH2:17]1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Komponenten

6

Edukt 2

HCID 3939Lithium HydroxideHCID 58080191(R)-Ethyl 4-(4-((tert-butyldimethylsilyloxy)(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)benzoate2×

Produkt 1

HCID 58080201(R)-4-(4-((tert-Butyldimethylsilyloxy)(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)benzoic acidAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium hydroxide (1.42 g, 59.29 mmol) was added to a mixture of (R)-ethyl 4-(4-((tert-butyldimethylsilyloxy)(4′-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)benzoate (INTERMEDIATE 12, 3.83 g, 6.78 mmol) in THF (27 ml), MeOH (9 ml) and water (1 ml). The resulting mixture was stirred at room temperature overnight and then the volatiles were removed under reduced pressure. The concentrate was purified by column chromatography (ISCO, 80 g silica column, eluting with 0→80% EtOAc/hexanes) to give the title product (3.24 g, yield: 89%).

Aufarbeitung

  1. customthe volatiles were removed under reduced pressure
  2. customThe concentrate was purified by column chromatography (ISCO, 80 g silica column, eluting with 0→80% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-35a46f3894ad44b1be4590b29f5c2406
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018381B2

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