Hydrochloric Acid → 2-((Cyclobutylmethyl)amino)ethanol
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[CH:1]1([C:5]([NH:7][CH2:8][C:9](OCC)=[O:10])=O)[CH2:4][CH2:3][CH2:2]1.Cl.ClCCl>O1CCCC1.CO>[NH3:7].[CH:1]1([CH2:5][NH:7][CH2:8][CH2:9][OH:10])[CH2:4][CH2:3][CH2:2]1[CH:1]1([C:5]([NH:7][CH2:8][C:9](OCC)=[O:10])=O)[CH2:4][CH2:3][CH2:2]1.Cl.ClCCl>O1CCCC1.CO>[NH3:7].[CH:1]1([CH2:5][NH:7][CH2:8][CH2:9][OH:10])[CH2:4][CH2:3][CH2:2]1
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):
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