Ammonium Chloride → 4'-(2-Fluoro-4-(4-pentylcyclohexyl)phenyl)bi(cyclohexane)-4-ol

HRID 1095240Notes

Reaction equation

HRID 1095240 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[CH:21]1[CH2:26][CH2:25][CH:24]([CH:27]2[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]2)[CH2:23][CH2:22]1.[H][H].[Cl-].[NH4+]>C(OCC)(=O)C>[F:3][C:4]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[CH:21]1[CH2:26][CH2:25][CH:24]([CH:27]2[CH2:28][CH2:29][CH:30]([OH:33])[CH2:31][CH2:32]2)[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 582122744'-[2-Fluoro-4-(4-pentyl-cyclohexyl)-phenyl]-bicyclohexyl-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 667814604'-(2-Fluoro-4-(4-pentylcyclohexyl)phenyl)bi(cyclohexane)-4-olYield 76.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (0.99 g) and Solmix (40 ml) were put in a reaction vessel under a nitrogen atmosphere, and cooled to 0° C. A Solmix solution in which 4′-[2-fluoro-4-(4-pentyl-cyclohexyl)-phenyl]-bicyclohexyl-4-one (6) (10.7 g) synthesized according to the method described in Example 1 was dissolved in Solmix (40 ml) was added dropwise thereto, with caution in the evolution of hydrogen gas, and the mixture was stirred for 3 hours. A saturated aqueous solution of ammonium chloride (200 ml) and ethyl acetate (200 ml) were added and mixed thereto. The mixture was then allowed to stand until it had separated into organic and aqueous phases, and an extractive operation to an organic phase was carried out. The organic phase was fractionated, and washed with brine, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified with a fractional operation by means of column chromatography using a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=5:1 by volume) as an eluent and silica gel as a stationary phase powder. The product was further purified by means of recrystallization from a mixed solvent of heptane and Solmix (heptane: Solmix=1:1 by volume), and dried, giving 8.2 g of 4′-(2-fluoro-4-(4-pentylcyclohexyl)phenyl)bi(cyclohexane)-4-ol (15). The yield based on the compound (6) was 76.6%.

Workup

  1. dissolutionwas dissolved in Solmix (40 ml)
  2. additionwas added dropwise
  3. additionmixed
  4. customhad separated into organic and aqueous phases
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe solution was concentrated under reduced pressure
  8. customthe residue was purified with a fractional operation by means of column chromatography
  9. customThe product was further purified by means of recrystallization from a mixed solvent of heptane and Solmix (heptane: Solmix=1:1 by volume)
  10. customdried

Sources & evidence

ORD record
ord-f29aaf83246348cc8775fa666bdfc03c
Source dataset
uspto-grants-2012_03
Patent number
US08137583B2

Reaction notes

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