Water → 3-Amino-3-[1-(4-chlorophenyl)cyclobutyl]propan-1-ol

HRID 1650974Notes

Reaction equation

HRID 1650974 reaction equation
[NH2:1][CH: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)[CH2:3][C:4](OCC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[NH2:1][CH:2]([C:9]1([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH2:12]1)[CH2:3][CH2:4][OH:5]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19823680Ethyl 3-amino-3-[1-(4-chlorophenyl)cyclobutyl]propanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 198238713-Amino-3-[1-(4-chlorophenyl)cyclobutyl]propan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl 3-amino-3-[1-(4-chlorophenyl)cyclobutyl]propanoate (5 g preapred as described in Example 137) in ether (25 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (3 g) in ether (50 ml). The mixture was heated under reflux for 3 hours, allowed to stand for 16 hours with no heating and then heated under reflux for a further 6 hours. Water (3 ml) was added dropwise with stirring to the cooled reaction mixture followed by 15% aqueous sodium hydroxide solution (3 ml) and water (9 ml). The reaction mixture was filtered and the residue washed with ether. The filtrate and the washings were combined, washed with water then brine and dried. Evaporation of the solvent gave a residue which was recrystallised from petroleum ether (b.p. 40°-60° C.) to give 3-amino-3-[1-(4-chlorophenyl)cyclobutyl]propan-1-ol (m.p. 98°-99° C.).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperaturewith no heating and then heated
  4. temperatureunder reflux for a further 6 hours
  5. filtrationThe reaction mixture was filtered
  6. washthe residue washed with ether
  7. washwashed with water
  8. dry with materialbrine and dried
  9. customEvaporation of the solvent
  10. customgave a residue which
  11. customwas recrystallised from petroleum ether (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-ae72017a50034231a990ee2f78c508dc
Source dataset
uspto-grants-1990_05
Patent number
US04925879

Reaction notes

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