2-Methyl-2-butanol → Sodium t-amyl oxide

860 mg of sodium were added to 18 ml of tertiary amylalcohol-absolute toluene (1:1), and the mixture was refluxed for 5 hours. Then, the reaction mixture was condensed to dryness, whereby sodium tertiary amyloxide was obtained. 20 ml of absolute toluene and 1.09 g of 1,2,3,4-tetrahydro-1-(3-methoxycarbonylpropyl)-2-benzyl-β-carboline were added to said sodium tertiary amyloxide under ice-cooling, and the mixture was stirred at the same temperature for 3 hours. After the reaction was completed, ethyl acetate was added to the reaction mixture. Said mixture was washed with an aqueous saturated sodium chloride solution, dried and then condensed. The residue thus obtained was purified by silica gel chromatography (Solvent: chloroform), and then recrystallized from a mixture of methanol and isopropyl ether, whereby 300 mg of 1,2,3,3a,4,5,6,7-octahydro-3-benzyl-7-oxo-azepino[1,2,3-lm]-β-carboline were obtained. Yield: 30.3%

1. temperaturethe mixture was refluxed for 5 hours
2. customcondensed to dryness

ORD record

ord-9a120aadb55e45dda52f5aeb8f85bc45

Source dataset

uspto-grants-1980_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04228168