Reaktion #166116

ord-436e06b4e72843c5bb0ba028063952e6

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
NCCc1ccc(F)cc1
2-(4-fluoro-phenyl)-ethylamine
→
O[C@@H]1C[C@@H](C(c2ccccc2)c2ccccc2)OC[C@H]1NCCc1ccc(F)cc1
(2S,4R,5R)-2-benzhydryl-5-[2-(4-fluorophenyl)-ethylamino]-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
NCCc1ccc(F)cc1
2-(4-fluoro-phenyl)-ethylamine

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 2-(4-fluoro-phenyl)-ethylamine (0.26 g, 1.88 mmol) in ethanol (Procedure E) to yield (2S,4R,5R)-2-benzhydryl-5-[2-(4-fluorophenyl)-ethylamino]-tetrahydropyran-4-ol, (−)-29c, 0.04 g (98%, [α]D=(−)62.9, c=1, MeOH).

Quelle

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