Hydrochloric Acid → HCID 178521562, compound

HRID 726500Notes

Reaction equation

HRID 726500 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[C@H:11]1[CH2:16][CH2:15][C@H:14]([CH:17]2[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2)[CH2:13][CH2:12]1.Cl>>[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[C@H:11]1[CH2:12][CH2:13][C@H:14]([C@H:17]2[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]2)[CH2:15][CH2:16]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 178516048HCID 178516048, compound

Product 1

HCID 178521562HCID 178521562, compoundYield 68.1%

Conditions

Temperature
-20 °C

Procedure

First, 40 ml of a mixed solvent (methanol/tetrahydrofuran=1/7) was placed in a 200 ml flask. The solvent was cooled to -20° C., and 0.55 g of sodium borohydride was added to the solvent. Separately, 2.1 g of 4-[trans-4-(2,3-difluorophenyl)cyclohexyl]cyclohexanone was dissolved in 30 ml of a mixed solvent (methanol/tetrahydrofuran=1/7). This solution was added dropwise to the previously prepared mixed solvent, and the resultant mixture was stirred overnight. Then, 5% diluted hydrochloric acid was added to the reaction mixture so as to make it acidic. Methanol was distilled away from the mixture under reduced pressure, and the residue was extracted with ethyl acetate. The solution thus obtained was washed with water and dried over anhydrous sodium sulfate, and a solvent was distilled away. Thereafter, the residue was purified by column chromatography (eluent: hexane/ethyl acetate=7/3 to 1/1) and recrystallized from methanol to obtain 1.44 g of trans-4-[trans-4-(2,3-difluorophenyl)cyclohexyl]cyclohexanol(Y: 67%). The compound thus obtained had a purity of 98.1% by GC.

Workup

  1. additionThis solution was added dropwise to the
  2. custompreviously prepared
  3. additionmixed solvent
  4. distillationMethanol was distilled away from the mixture under reduced pressure
  5. extractionthe residue was extracted with ethyl acetate
  6. customThe solution thus obtained
  7. washwas washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationa solvent was distilled away
  10. customThereafter, the residue was purified by column chromatography (eluent: hexane/ethyl acetate=7/3 to 1/1)
  11. customrecrystallized from methanol

Sources & evidence

ORD record
ord-bb7be1fa156041b985a8d7cbe4c7b050
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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