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Lithium Hydroxide → (S)-4-(4-((4'-Chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)benzoic acid

HRID 1476304
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1476304
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C@@H:14]([OH:32])[CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C@@H:14]([OH:32])[CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:30][CH:31]=3)[CH2:17][CH2:16]2)=[CH:6][CH:7]=1
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Komponenten

6

Edukt 2

HCID 3939Lithium HydroxideHCID 56650672(S)-Ethyl 4-(4-((4'-chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)benzoate2×

Produkt 1

HCID 58080142(S)-4-(4-((4'-Chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(S)-Ethyl 4-(4-((4′-chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)benzoate (INTERMEDIATE 11B, 150.0 mg, 0.33 mmol) was dissolved in THF (6.0 ml) and methanol (1.4 ml). A solution of LiOH (40.6 mg) in water (1.4 ml) was added. The solution was heated at 50° overnight. The reaction mixture was allowed to cool to room temperature and then concentrated under reduced pressure. The residue was diluted with water (5 ml), acidified with 1N aq. HCl (2.0 ml), and extracted with DCM (2×5 ml). The extract was dried (MgSO4), filtered through cotton, and evaporated under vacuum to provide the title product as a substantially separated enantiomer (155 mg, yield: almost quantitative) 1H NMR (400 MHz, DICHLOROMETHANE-d2) δ ppm 0.79-0.94 (m, 1 H) 0.98-1.12 (m, 1 H) 1.14-1.40 (m, 4 H) 2.04 (m, 1 H) 2.67 (td, J=12.51, 2.78 Hz, 1 H) 2.78 (td, 1 H) 3.74 (d, 1 H) 3.91 (m, 1 H) 4.48 (d, 1 H) 6.81 (d, 2 H) 7.17-7.29 (m, 3 H) 7.31-7.49 (m, 4 H) 7.61 (dd, 1 H) 7.84-7.93 (m, 2 H).

Aufarbeitung

  1. temperatureThe solution was heated at 50° overnight
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water (5 ml)
  4. extractionextracted with DCM (2×5 ml)
  5. dry with materialThe extract was dried (MgSO4)
  6. filtrationfiltered through cotton
  7. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-36c83ba63fa24301bc38db7c6ea12af3
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09018381B2

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