Methyl morpholine oxide → 1-(6-Isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-ethanol

HRID 1582084Notes

Reaction equation

[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([CH:16]([CH3:18])[CH3:17])=[CH:10][C:11]=2[CH:13]([OH:15])[CH3:14])[C:6]([CH3:20])([CH3:19])[CH2:5][CH2:4]1)[CH3:2].[CH3:21][N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH:16]([C:9]1[CH:8]=[C:7]2[C:12](=[C:11]([CH:13]([OH:15])[CH3:14])[CH:10]=1)[N:3]([CH2:1][CH2:2][CH3:21])[CH2:4][CH2:5][C:6]2([CH3:20])[CH3:19])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-ethan-1-ol (Intermediate 9, 1.50 g, 6.33 mmol) in 15 ml of CH2Cl2 at 0° C. was added 4-methylmorpholine N-oxide (1.48 g, 12.7 mmol), tetrapropylammonium perruthenate (333 mg, 0.95 mmol), and 4 Å molecular sieve powder (150 mg). The mixture was stirred at 0° C. and allowed to warm gradually while being monitored carefullly. As soon as the temperature rose to 25° C., the reaction was re-cooled in an ice bath. The crude mixture was immediately loaded onto a pre-packed silica gel column. The column was first eluted with 100% hexane, and then with 5% ethyl acetate and hexane to yield the title compound as a yellow oil.

Workup

temperatureto warm gradually
customrose to 25° C.
temperaturethe reaction was re-cooled in an ice bath
washThe column was first eluted with 100% hexane

Sources & evidence

ORD record: ord-9b80b50fca564bfdaf5e67eccf2e8692
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734193B1

Reaction notes

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