Hydrochloric Acid → 2-((Cyclobutylmethyl)amino)ethanol

Temperature

60 °C

Ethyl N-(cyclobutylcarbonyl)glycinate (7.6 g, 41 mmol) in tetrahydrofuran (40 ml) was added to borane-tetrahydrofuran complex (100 ml of a 1.0 N solution in tetrahydrofuran, 100 mol) and heated at 60° C. for 24 hours. Additional borane-tetrahydrofuran complex (20 ml) was added to the mixture and heating continued for a further 8 hours. The reaction mixture was then diluted slowly with methanol (20 ml) and stirred at ambient temperature for 0.5 hour. A concentrated solution of hydrochloric acid (6 ml) was slowly added following dilution with dichloromethane. The solid which precipitated was removed by filtration and washed with dichloromethane. The organic phase was dried (magnesium sulphate), concentrated and purified by chromatography on silica gel. Elution with dichloromethane:methanol (96:4) then dichloromethane:methanolic ammonia (94:6) yielded 2-((cyclobutylmethyl)amino)ethanol (4.16 g, 78% yield):

1. additionAdditional borane-tetrahydrofuran complex (20 ml) was added to the mixture
2. temperatureheating
3. customThe solid which precipitated
4. customwas removed by filtration
5. washwashed with dichloromethane
6. dry with materialThe organic phase was dried (magnesium sulphate)
7. concentrationconcentrated
8. custompurified by chromatography on silica gel
9. washElution with dichloromethane:methanol (96:4)

ORD record

ord-47fc1d899b1c4cc191f955c025a51dfa

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402585B2