Reaktion #694194

ord-a28795b2e1ef49e99c5ea1c36d1b9bae

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
COc1cc(CN)cc(OC)c1
3,5-dimethoxybenzylamine
→
COc1cc(CN[C@@H]2CO[C@H](C(c3ccccc3)c3ccccc3)C[C@H]2O)cc(OC)c1
(2S, 4R, 5R)-2-benzhydryl-5-(3,5-dimethoxy-benzylamino)-tetrahydropyran-4-ol
Ausbeute 95.0%

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
COc1cc(CN)cc(OC)c1
3,5-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 3,5-dimethoxybenzylamine (0.25 g, 1.50 mmol) (Procedure E) to yield (2S, 4R, 5R)-2-benzhydryl-5-(3,5-dimethoxy-benzylamino)-tetrahydropyran-4-ol, (−)-29f, 0.03 g (Yield; 95%, [α]D=(−)58.60, c=1, CHCl3).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07915433B2uspto-grants-2011_03