Ammonia → 1-[1-(4-Chlorophenyl)cyclobutyl]-3-ethyl-1-iminopentan-3-ol

HRID 728277Notes

Reaction equation

HRID 728277 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:14](=[N:22]O)[CH2:15][C:16]([CH2:20][CH3:21])([OH:19])[CH2:17][CH3:18])[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.O.N>COCCOC.[Ti](Cl)(Cl)(Cl)Cl>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:14](=[NH:22])[CH2:15][C:16]([CH2:20][CH3:21])([OH:19])[CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13]2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 4311764Sodium borohydrideHCID 867439391-[1-(4-Chlorophenyl)cyclobutyl]-3-ethyl-3-hydroxypentan-1-one oxime

Product 1

HCID 198237421-[1-(4-Chlorophenyl)cyclobutyl]-3-ethyl-1-iminopentan-3-ol

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Titanium (IV) chloride (3.9 ml) was added dropwise to stirred dry 1,2-dimethoxyethane (68 ml) cooled to 0° C. under nitrogen. The temperature was maintained at 0° C. and powdered sodium borohydride (2.7 g) was added. A solution of 1-[1-(4-chlorophenyl)cyclobutyl]-3-ethyl-3-hydroxypentan-1-one oxime (5.2 g) in dry 1,2-dimethoxyethane (17 ml) was then added dropwise under nitrogen and the mixture stirred for 30 minutes at 0° C. and then at ambient temperature for 14 hours. After cooling the mixture to 0° C., water (170 ml) was added dropwise and the mixture basified with aqueous ammonia solution (S.G. 0.880) with cooling. The resulting solution was extracted with ether and the extracts washed with brine and dried. Removal of the solvents by evaporation in vacuo gave an oil which was distilled (b.p. 150/0.05 mm) to give 1-[1-(4-chlorophenyl)cyclobutyl]-3-ethyl-1-iminopentan-3-ol.

Workup

  1. temperatureThe temperature was maintained at 0° C.
  2. waitat ambient temperature for 14 hours
  3. temperatureAfter cooling the mixture to 0° C.
  4. temperaturewith cooling
  5. extractionThe resulting solution was extracted with ether
  6. washthe extracts washed with brine
  7. customdried
  8. customRemoval of the solvents
  9. customby evaporation in vacuo
  10. customgave an oil which
  11. distillationwas distilled (b.p. 150/0.05 mm)

Sources & evidence

ORD record
ord-5f3d7908594d472cb1b9352b1e97385d
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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