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

HRID 749171
Notes
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Reaction equation

HRID 749171 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6344Dichloromethane2×HCID 60810545N-(Cyclobutylcarbonyl)glycine ethyl ester

Product 2

HCID 222AmmoniaHCID 183163062-((Cyclobutylmethyl)amino)ethanolYield 157.1%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

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):

Workup

  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)

Sources & evidence

ORD record
ord-47fc1d899b1c4cc191f955c025a51dfa
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07402585B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes