Sodium borohydride → hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one

HRID 637769Notes

Reaction equation

HRID 637769 reaction equation
CC(C)(CCCC)C=CC([CH:7]1[CH:14]2[CH:10]([O:11][C:12](=[O:15])[CH2:13]2)[CH2:9][CH:8]1[CH3:16])=O.[BH4-].[Na+]>>[CH3:16][CH:8]1[CH2:9][CH:10]2[O:11][C:12](=[O:15])[CH2:13][CH:14]2[CH2:7]1

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 731845924-(4,4-dimethyl-1-oxo-2-octenyl)hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one

Product 1

HCID 12383287hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one

Procedure

The crude, optically active (3aR,4S,-5R,6aS)-[S*,R*(E)]-4-(4,4-dimethyl-1-oxo-2-octenyl)hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one (11.1 g) was reduced with sodium borohydride (1.1 g) as described in Example V. After workup 10.45 g (93%) of optically active [3aR-[3aalpha,4alpha(1S*,2E),5beta,6aalpha]]-4-[1-(hydroxy)-4,4-dimethyl)-2-octenyl]hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one was obtained as a viscous, amber colored oil. The product gave a single spot on TLC and was used as is in Examples XVI through XXIV of the synthesis.

Sources & evidence

ORD record
ord-7e3686a2081f465dbd01818fd50f0ac9
Source dataset
uspto-grants-1985_12
Patent number
US04558140

Reaction notes

Loading…