Trifluoroacetic acid → Methyl 8-bromo-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate

Temperatur

65 °C

To a solution of methyl 8-bromo-1-(4-methoxybenzyl)-1,2,3,4-terahydro-1-benzoazocine-5-carboxylate (10.0 g), in toluene (50 ml) was added trifluoroacetic acid (50 ml), and the mixture was stirred at 65° C. for 2 hours. After distilling off the solvent under reduced pressure, water was added at 0° C. and the reaction mixture was neutralized with potassium carbonate and extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium bicarbonate solution and saturated brine, after which it was dried with magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=9:1). The resulting solid was washed with hexane to give methyl 8-bromo-1,2,3,4-terahydro-1-benzoazocine-5-carboxylate (6.59 g) as yellow crystals.

1. distillationAfter distilling off the solvent under reduced pressure, water
2. additionwas added at 0° C.
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with aqueous saturated sodium bicarbonate solution and saturated brine
5. dry with materialafter which it was dried with magnesium sulfate
6. distillationThe solvent was distilled off under reduced pressure
7. customthe resulting residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=9:1)
8. washThe resulting solid was washed with hexane

ORD-Eintrag

ord-758902147d4c42b7b193f6a7737c475a

Quelldatensatz

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08362058B2