3,3-Dimethyl-1,2,3,4-tetrahydroquinoxalin-2-one → (4aR,8aS)-3,3-Dimethyloctahydroquinoxalin-2(1H)-one

HRID 986339Notes

Reaction equation

HRID 986339 reaction equation
[CH3:1][C:2]1([CH3:13])[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12]>[Rh]>[CH3:1][C:2]1([CH3:13])[NH:11][C@H:10]2[C@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[NH:4][C:3]1=[O:12]

Participants

3

Reactant 1

HCID 5952033,3-Dimethyl-1,2,3,4-tetrahydroquinoxalin-2-one

Product 1

HCID 12886757(4aR,8aS)-3,3-Dimethyloctahydroquinoxalin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

In a manner analogous with the foregoing, 3,3-dimethyl-3,4-dihydroquinoxalin-2-one is hydrogenated at about 130° C. and 1500 psi in the presence of rhodium (5%) on charcoal in 2 hours, to yield cis-3,3-dimethyl-decahydroquinoxalin-2-one.

Workup

  1. customis hydrogenated at about 130° C.

Sources & evidence

ORD record
ord-924e105ede204f6ca0ad6d7321125672
Source dataset
uspto-grants-1987_12
Patent number
US04711957

Reaction notes

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