Hydrochloric Acid → HCID 13075561, compound

HRID 2295993Notes

Reaction equation

HRID 2295993 reaction equation
[C:1]([CH2:3][CH:4]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:5]([N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)[C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8])#[N:2].[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>C(O)(C)C>[C:1]([CH2:3][CH:4]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:5]([N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)[CH:6]([OH:11])[C:7]([CH3:10])([CH3:9])[CH3:8])#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 13075560HCID 13075560, compound

Product 1

HCID 13075561HCID 13075561, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

96.5 (0.33 mole) of 6-cyano-2,2-dimethyl-4-imidazol-1-yl-5-phenyl-3-hexanone (obtained as described in Example 1) were dissolved in 400 ml of isopropanol, and 15.12 g (0.4 mole) of sodium borohydride were added in portions at 0° to 20° C. The mixture was subsequently stirred at room temperature for 24 hours, 800 ml of 2 N hydrochloric acid were added dropwise at 0° to 10° C. and the mixture was subsequently stirred again at room temperature for 24 hours. The reaction mixture was then neutralized with 1.5 liters of saturated sodium bicarbonate solution and extracted three times with 400 ml of methylene chloride each time. The combined organic phases were washed with water, dried over sodium sulphate and concentrated. The residue was boiled up in 300 ml of diisopropyl ether, and the crystals formed on cooling were filtered off. 28.7 g (30% of theory) of 6-cyano-2,2-dimethyl-4-imidazol-1-yl-5-phenyl-3-hexanol were obtained as a diastereomer mixture of melting point 212° to 228° C.

Workup

  1. stirringthe mixture was subsequently stirred again at room temperature for 24 hours
  2. extractionextracted three times with 400 ml of methylene chloride each time
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customthe crystals formed
  7. temperatureon cooling
  8. filtrationwere filtered off

Sources & evidence

ORD record
ord-7de39c934149429b965fe22f0022fe72
Source dataset
uspto-grants-1984_01
Patent number
US04427673

Reaction notes

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