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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence