Reaktion #694184

ord-5fcfc00b2017408d9b0094ea6e9c6550

Reaktionsgleichung

c1ccc(C(c2ccccc2)[C@H]2C[C@@H]3O[C@@H]3CO2)cc1
(1R, 4R, 6S)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane
COc1ccc(CN)cc1
p-methoxybenzylamine
→
COc1ccc(CN[C@H]2CO[C@@H](C(c3ccccc3)c3ccccc3)C[C@@H]2O)cc1
(2R, 4S, 5S)-2-benzhydryl-5-(4-methoxy-benzylamino)-tetrahydropyran-4-ol
Ausbeute 80.0%

Edukte

c1ccc(C(c2ccccc2)[C@H]2C[C@@H]3O[C@@H]3CO2)cc1
(1R, 4R, 6S)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane
COc1ccc(CN)cc1
p-methoxybenzylamine

Reagenzien

Keine

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

(1R, 4R, 6S)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane 28c (0.02 g, 0.075 mmol) was reacted with p-methoxybenzylamine (0.21 g, 1.50 mmol) in ethanol (Procedure E) to yield (2R, 4S, 5S)-2-benzhydryl-5-(4-methoxy-benzylamino)-tetrahydropyran-4-ol (+)-29a 0.024 g (80%, [α]D=(+)72.8, c=1, MeOH). The 1HNMR and 13CNMR were identical with (2S, 4R, 5R)-2-benzhydryl-5-(4-methoxy-benzylamino)-tetrahydropyran-4-ol.

Quelle

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