Acetic Acid → Ethyl 3-amino-3-[1-(4-chlorophenyl)cyclobutyl]propanoate

HRID 1650958Notes

Reaction equation

HRID 1650958 reaction equation
[NH2:1][C:2]([C:9]1([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C([BH3-])#N.[Na+].C([O-])(=O)C.[NH4+].C(O)(=O)C>C(O)C>[NH2:1][CH:2]([C:9]1([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[CH2:10][CH2:11][CH2:12]1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 67945594Ethyl 3-amino-3-[1-(4-chlorophenyl)cyclobutyl]acrylate

Product 1

HCID 19823680Ethyl 3-amino-3-[1-(4-chlorophenyl)cyclobutyl]propanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-amino-3-[1-(4-chlorophenyl)cyclobutyl]acrylate (90 g), sodium cyanoborohydride (36 g), ammonium acetate (27 g) and acetic acid (60 ml) in ethanol (1.5 liters) was allowed to stand at room temperature for 5 days and then concentrated to 600 ml and poured into water (2.5 liters). The aqueous solution was basified, extracted with ether and the ether extract back extracted with 2N hydrochloric acid. The acidic aqueous extract was cooled with ice, basified and extracted with ether and the extract dried and evaporated to give ethyl 3-amino-3-[1-(4-chlorophenyl)cyclobutyl]propanoate.

Workup

  1. concentrationconcentrated to 600 ml
  2. additionpoured into water (2.5 liters)
  3. extractionextracted with ether
  4. extractionthe ether extract back
  5. extractionextracted with 2N hydrochloric acid
  6. extractionThe acidic aqueous extract
  7. temperaturewas cooled with ice
  8. extractionextracted with ether
  9. customthe extract dried
  10. customevaporated

Sources & evidence

ORD record
ord-850120fe180741d289644311f4be719c
Source dataset
uspto-grants-1990_05
Patent number
US04925879

Reaction notes

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