Water → (1R*,2R*,5R*)-8-Benzyl-2-[(2-methoxy-5-trifluoromethoxyphenyl)methoxy]-1-phenyl-8-azabicyclo[3.2.1]octane

HRID 2088135

Reaktionsgleichung

Reaktionsgleichung von HRID 2088135
[CH2:1]([N:8]1[C@@H:13]2[CH2:14][CH2:15][C@@:9]1([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@H:10]([OH:16])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][C:28]=1[CH2:29]Br.O>C1COCC1>[CH2:1]([N:8]1[C@@H:13]2[CH2:14][CH2:15][C@@:9]1([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@H:10]([O:16][CH2:29][C:28]1[CH:31]=[C:32]([O:35][C:36]([F:37])([F:38])[F:39])[CH:33]=[CH:34][C:27]=1[O:26][CH3:25])[CH2:11][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 37237722-Methoxy-5-(trifluoromethoxy)benzyl bromideHCID 69688994(1R*,2R*,5R*)-8-Benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol

Produkt 1

HCID 69889714(1R*,2R*,5R*)-8-Benzyl-2-[(2-methoxy-5-trifluoromethoxyphenyl)methoxy]-1-phenyl-8-azabicyclo[3.2.1]octane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(1R*,2R*,5R*)-8-Benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol (Description 9; 348 mg, 1.19 mmol) was dissolved in THF then sodium hydride (71 mg, 60% in oil, 1.79 mmol) added and the reaction mixture stirred for 10 minutes. 2-methoxy-5-trifluoromethoxybenzyl bromide was added and the reaction mixture stirred at 50° C. for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate (×3), dried (MgSO4) and concentrated in vacuo to give a yellow oil. This was purified by flash column chromatography [5%-15% ethyl acetate in iso-hexane] to give the title compound. (205 mg, 35%).

Aufarbeitung

  1. stirringthe reaction mixture stirred at 50° C. for 2 hours
  2. extractionextracted with ethyl acetate (×3)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a yellow oil
  6. customThis was purified by flash column chromatography [5%-15% ethyl acetate in iso-hexane]

Quellen und Nachweise

ORD-Eintrag
ord-9525a5aa9d7b4765814a084206cffb1a
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727249B2

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