Reaktion #166118

ord-088e71edff4741ad92f47adb97670064

Reaktionsgleichung

c1ccc(C(c2ccccc2)[C@@H]2C[C@@H]3O[C@@H]3CO2)cc1
(1R,4S,6S)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]heptane
c1ccc(C(c2ccccc2)[C@@H]2C[C@@H]3O[C@@H]3CO2)cc1
(1R,4S,6S)-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,4R,6S)-6-benzhydryl-4-benzylamino-tetrahydropyran-3-ol
Ausbeute 86.0%

Edukte

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

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

(1R,4S,6S)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]heptane 28b (0.03 g, 0.09 mmol) reacted with benzylamine (0.20 g, 1.88 mmol) (Procedure E) to yield (3S,4R,6S)-6-benzhydryl-4-benzylamino-tetrahydropyran-3-ol, (−)-29h, 0.03 g (Yield; 86%), [α]D=(−)70.6, c=1, MeOH).

Quelle

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