Reaktion #166113

ord-d08d6c059bec4678851135c7de8133f0

Reaktionsgleichung

c1ccc(C(c2ccccc2)[C@H]2C[C@H]3O[C@H]3CO2)cc1
(1S,4R,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]heptane
c1ccc(C(c2ccccc2)[C@H]2C[C@H]3O[C@H]3CO2)cc1
(1S,4R,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane
NCc1ccccc1
benzylamine
→
O[C@@H]1CO[C@@H](C(c2ccccc2)c2ccccc2)C[C@@H]1NCc1ccccc1
(3S,4S,6R)-6-benzhydryl-4-benzylamino-tetrahydropyran-3-ol

Edukte

c1ccc(C(c2ccccc2)[C@H]2C[C@H]3O[C@H]3CO2)cc1
(1S,4R,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]heptane
c1ccc(C(c2ccccc2)[C@H]2C[C@H]3O[C@H]3CO2)cc1
(1S,4R,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane
NCc1ccccc1
benzylamine

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

(1S,4R,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]heptane 28d (0.019 g, 0.071 mmol) was reacted with benzylamine (0.15 g, 1.43 mmol) (Procedure E) to yield (3S,4S,6R)-6-benzhydryl-4-benzylamino-tetrahydropyran-3-ol, (+)-29h, 0.023 (85%, [α]D=(+)70.1, c=1, MeOH).

Quelle

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