Methyl morpholine oxide → (E)-2-Fluoro-3-(6-isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-but-2-en-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-3-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-2-fluoro-but-2-en-1-ol (Intermediate 18, 133 mg, 0.35 mmol) in 2 ml of CH2Cl2 at 0° C. was added 4-methylmorpholine N-oxide (83 mg, 0.71 mmol), tetrapropylammonium perruthenate (18.6 mg, 0.05 mmol), and 4 Å molecular sieve powder (10 mg). The mixture was stirred at 0° C. for 5 min, and the bath was removed. The temperature of reaction mixture was monitored carefully, and as soon as the temperature rose to 25° C., the reaction was re-cooled in an ice bath. The cooled reaction mixture was loaded onto a pre-packed silica gel column, and the product was eluted with 100% hexane followed by 2% ethyl acetate in hexane to yield the title compound as a bright yellow solid.

Provenance & Evidence