Reaktion #166120

ord-22dcb1bb240e43bb864e6800b112c1a5

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
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
COc1ccc(CN)c(OC)c1
2,4-dimethoxybenzylamine
→
COc1ccc(CN[C@@H]2CO[C@H](C(c3ccccc3)c3ccccc3)C[C@H]2O)c(OC)c1
(2S,4R,5R)-2-benzhydryl-5-(2,4-dimethoxybenzylamino)-tetrahydropyran-4-ol
Ausbeute 70.0%

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
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
COc1ccc(CN)c(OC)c1
2,4-dimethoxybenzylamine

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

(1S,4S,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]heptane 28a (0.020 g, 0.075 mmol) was reacted with 2,4-dimethoxybenzylamine (0.25 g, 1.50 mmol) (Procedure E) to yield (2S,4R,5R)-2-benzhydryl-5-(2,4-dimethoxybenzylamino)-tetrahydropyran-4-ol, (−)-29e, 0.025 g (Yield; 70%, [α]D=(−)3.70, c=1, CHCl3).

Quelle

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