Hydrochloric Acid → cis-3-(Benzyloxy)cyclobutanamine

HRID 1846755Notes

Reaction equation

HRID 1846755 reaction equation
Cl.[CH2:2]([O:9][CH:10]1[CH2:13][CH:12]([NH:14]C(=O)OC(C)(C)C)[CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1COCC1>[CH2:2]([O:9][CH:10]1[CH2:13][CH:12]([NH2:14])[CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53415284tert-Butyl [3-(benzyloxy)cyclobutyl]carbamate

Product 1

HCID 12104169cis-3-(Benzyloxy)cyclobutanamineYield 87.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

HCl (5-6 N in IPA, 3 mL) was added to a solution of tert-butyl 3-(benzyloxy)cyclobutylcarbamate (1.07 g, 3.86 mmol) in THF (10 mL). The mixture was stirred at 50° C. for 3 h, then cooled to RT. The solvent was removed in vacuo and EtOAc (10 mL) was added. The resulting suspension was cooled to 0° C. for 1 h, then the solid was collected by filtration to give the amine as a white solid (601 mg, 73%).

Workup

  1. temperaturecooled to RT
  2. customThe solvent was removed in vacuo and EtOAc (10 mL)
  3. additionwas added
  4. temperatureThe resulting suspension was cooled to 0° C. for 1 h
  5. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-35503805b3cb4e4798b819d94a55e881
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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