Hydrogen Peroxide → HCID 22799507, compound

Participants

Reaction Conditions

Reaction Steps

1-Phenyl-8-[(1,2,3,4-tetrahydro-6-methoxy-1-oxo-2-naphthalenyl)methyl]-1,3,8-triazaspiro[4.5]decan-4-one (5.4 g) dissolved in 60 ml of dry tetrahydrofuran is added dropwise to a flask charged with 2.1 equivalents of a 1 molar tetrahydrofuran solution of lithium tri-sec-butylborohydride which has been cooled to -78° C under an argon atmosphere. The resulting solution is stirred for 16 hours at room temperature. The reaction mixture is treated at 0° C with 15 ml of 3 molar sodium hydroxide followed by the addition of 15 ml of 30% hydrogen peroxide. The aqueous phase is saturated with potassium carbonate and the organic layer is separated and concentrated. The residue is dissolved in methylene chloride, washed with water, dried and concentrated producing the crude product. Two crystallizations of this material from absolute ethanol/methylene chloride yield 3.8 g of isomerically pure title compound, melting point 182°-183° C.

Provenance & Evidence