2-Benzhydryl-3-quinuclidinone → (2S,3S)-2-benzhydrylquinuclidin-3-ol

HRID 409651

Reaktionsgleichung

Reaktionsgleichung von HRID 409651
[CH:1]([CH:14]1[C:19](=[O:20])[CH:18]2[CH2:21][CH2:22][N:15]1[CH2:16][CH2:17]2)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[H][H]>CC(O)C>[CH:1]([C@H:14]1[C@@H:19]([OH:20])[CH:18]2[CH2:17][CH2:16][N:15]1[CH2:22][CH2:21]2)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 4251102-Benzhydryl-3-quinuclidinoneHCID 23665647Potassium tert-butoxideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 10613679(2S,3S)-2-benzhydrylquinuclidin-3-olAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Versuchsvorschrift

397.7 mg (1.30 mmol) of a racemic mixture of 2-benzhydrylquinuclidin-3-one (1-2) and 1.2 mg (1.3 μmol) of (S)-1,1′-binaphthyl-2,2′-bis(diphenyl)phosphine ruthenium (II) dichloride (R,R)-hexane-2,5-diamine complex were placed in an autoclave in which the inside had been replaced with argon. After adding 6.4 ml of 2-propanol thereto and degassing, 0.13 mL (0.13 mmol) of a 2-propanol solution of potassium tert-butoxide (1.0 M) were added thereto followed by stirring for 18 hours at 20 to 25° C. at a hydrogen pressure of 1.0 MPa. After concentrating the reaction solution, analysis of the crude purification product by 1H-NMR indicated that only the syn form had been formed. The reaction solution was then purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=3:1 (volume ratio)) to obtain 382 mg (1.30 mmol, yield: 96%) of (2S,3S)-2-benzhydrylquinuclidin-3-ol (3-2). The optical purity of this substance as measured by high-performance liquid chromatography (eluent: acetonitrile:0.02 M aqueous disodium hydrogen phosphate=6:4 (volume ratio), column: CHIRALCEL OD-RH, Daicel Chemical Industries, Ltd.) was 96% ee.

Aufarbeitung

  1. customdegassing
  2. concentrationAfter concentrating the reaction solution, analysis of the crude
  3. custompurification product
  4. customhad been formed
  5. customThe reaction solution was then purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=3:1 (volume ratio))

Quellen und Nachweise

ORD-Eintrag
ord-b433acb6fa6442b0bfa4001f4fd3e314
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759524B2

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