(1S,5R)-3-(3-{[(1,1-Dimethylethyl)(Dimethyl)Silyl]Oxy}Propyl)-1-[2-Fluoro-4-(Trifluoromethyl)Phenyl]-3-Azabicyclo[3.1.0]Hexane → 3-{(1S,5R)-1-[2-Fluoro-4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}-1-propanol

HRID 254445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 254445
CC([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][N:10]1[CH2:15][C@H:14]2[C@:12]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=3[F:26])([CH2:13]2)[CH2:11]1)(C)C>C1COCC1>[F:26][C:17]1[CH:18]=[C:19]([C:22]([F:25])([F:23])[F:24])[CH:20]=[CH:21][C:16]=1[C@:12]12[CH2:13][C@H:14]1[CH2:15][N:10]([CH2:9][CH2:8][CH2:7][OH:6])[CH2:11]2

Komponenten

3

Edukt 1

HCID 59759997(1S,5R)-3-(3-{[(1,1-Dimethylethyl)(Dimethyl)Silyl]Oxy}Propyl)-1-[2-Fluoro-4-(Trifluoromethyl)Phenyl]-3-Azabicyclo[3.1.0]Hexane

Produkt 1

HCID 597599943-{(1S,5R)-1-[2-Fluoro-4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}-1-propanolAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To (1S,5R)-3-(3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}propyl)-1-[2-fluoro-4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (135 mg, 0.3 mmol) HCl (1N, 2 mL) was added followed by THF (2 mL) and the reaction mixture was stirred at r.t. for 1 h. The reaction mixture was concentrated under vacuum and the solid was washed with Et2O (3×10 ml), dissolved in MeOH (2 mL) and eluted through SCX cartridge (eluent: NH3, 0.5 M in MeOH) to give 86 mg of the title compound.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. washthe solid was washed with Et2O (3×10 ml)
  3. dissolutiondissolved in MeOH (2 mL)
  4. washeluted through SCX cartridge (eluent: NH3, 0.5 M in MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-b04e4d326b8542b0aeea00999535336b
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875643B2

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