Reaktion #166130

ord-fcfe9bf1d5cc463d8fc7a238c231772d

Reaktionsgleichung

c1ccc(C(c2ccccc2)[C@H]2C[C@H]3O[C@H]3CO2)cc1
(1S,4R,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,4R,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
C1COCCOCCOCCO1
12-crown-4 ether
→
O[C@@H]1CC[C@H](C(c2ccccc2)c2ccccc2)OC1
(3R,6R)-6-benzhydryl-tetrahydropyran-3-ol
Ausbeute 77.0%

Edukte

c1ccc(C(c2ccccc2)[C@H]2C[C@H]3O[C@H]3CO2)cc1
(1S,4R,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,4R,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
C1COCCOCCOCCO1
12-crown-4 ether

Reagenzien

Keine

Lösungsmittel

CCCCC
pentane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Treatment of (1S,4R,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]heptane 28d (0.06 g, 0.23 mmol) with a suspension of LiAlH4 (0.06 g, 1.58 mmol) in pentane along with 12-crown-4 ether (0.31 g, 1.74 mmol) for 15 h at room temperature afforded (3R,6R)-6-benzhydryl-tetrahydropyran-3-ol 38 0.046 g (77%, [α]D=(+)74.9, c=1, MeOH).

Quelle

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