Reaktion #166129

ord-5822be276e24439c935abf218252ab2f

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
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
→
O[C@H]1CC[C@H](C(c2ccccc2)c2ccccc2)OC1
trans-(3S,6R)-6-benzhydryl-tetrahydro-pyran-3-ol
Ausbeute 70.0%
O[C@H]1CC[C@H](C(c2ccccc2)c2ccccc2)OC1
(3S,6R)-6-benzhydryl-tetrahydropyran-3-ol
Ausbeute 70.0%

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
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4

Reagenzien

Keine

Lösungsmittel

CCCCC
pentane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

(1R,4R,6S)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane (0.05 g, 0.19 mmol) was treated with LiAlH4 (0.036 g, 0.94 mmol) (Procedure I) in dry pentane to yield trans-(3S,6R)-6-benzhydryl-tetrahydro-pyran-3-ol 33b 0.035 g (70%, [α]D=(+)61.7, c=1, MeOH).

Quelle

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