Triethylamine → Methyl 8-{[(5-bromo-2-methylphenyl)acetyl]amino}-1,4-dioxaspiro[4.5]decane-8-carboxylate

At room temperature, 5.47 g (25.41 mmol) of methyl 8-amino-1,4-dioxaspiro[4.5]decane-8-carboxylate [T. Satoh et al., Tetrahedron 63 (2007), 4806-4813], 3.86 g (38.12 mmol) of triethylamine and 155 mg (1.27 mmol) of N,N-dimethylaminopyridine were dissolved in 45 ml of dichloromethane. A solution of 6.29 g (25.41 mmol) of (5-bromo-2-methylphenyl)acetyl chloride (Example 3A) in 45 ml of dichloromethane was then added dropwise to the mixture. The resulting reaction mixture was stirred at room temperature overnight. For work-up, the mixture was diluted with dichloromethane and the organic phase was washed with aqueous saturated sodium bicarbonate solution. After drying over sodium sulphate, the mixture was concentrated by evaporation and the residue was purified by chromatography on silica gel (mobile phase: hexane/ethyl acetate gradient/1% triethylamine) Evaporation and drying gave 3.64 g (34% of theory) of the title compound which was used without further characterization in the next step.

1. customThe resulting reaction mixture
2. washthe organic phase was washed with aqueous saturated sodium bicarbonate solution
3. dry with materialAfter drying over sodium sulphate
4. concentrationthe mixture was concentrated by evaporation
5. customthe residue was purified by chromatography on silica gel (mobile phase: hexane/ethyl acetate gradient/1% triethylamine) Evaporation
6. customdrying

ORD-Eintrag

ord-9fea5488ddf540c19d5aef1337df0d66

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09278925B2