Reaktion #166114

ord-c09801b31ea644a3a7cee90af5e07934

Reaktionsgleichung

c1ccc(C(c2ccccc2)[C@@H]2C[C@H]3O[C@H]3CO2)cc1
(1S,4S,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane
NCc1ccc(F)cc1
para-fluoro-benzylamine
→
O[C@@H]1C[C@@H](C(c2ccccc2)c2ccccc2)OC[C@H]1NCc1ccc(F)cc1
(2S,4R,5R)-2-benzhydryl-5-(4-fluoro-benzylamino)-tetrahydropyran-4-ol

Edukte

c1ccc(C(c2ccccc2)[C@@H]2C[C@H]3O[C@H]3CO2)cc1
(1S,4S,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane
NCc1ccc(F)cc1
para-fluoro-benzylamine

Reagenzien

Keine

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

(1S,4S,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane 28a (0.025 g, 0.094 mmol) was reacted with para-fluoro-benzylamine (0.24 g, 1.88 mmol) in ethanol (Procedure E) to yield (2S,4R,5R)-2-benzhydryl-5-(4-fluoro-benzylamino)-tetrahydropyran-4-ol, (−)-29b, 0.032 g (86%, [α]D=(−)77.2, c=1, MeOH).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08841464B2uspto-grants-2014_09