Ammonia → HCID 178444949, compound

HRID 2088243Notes

Reaction equation

HRID 2088243 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C@H:20]2[CH2:25][CH2:24][C@H:23]([CH:26]=[O:27])[CH2:22][CH2:21]2)=[C:16]([F:28])[C:15]=1[F:29])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(OCC)(=O)C.N>C1COCC1>[CH2:7]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C@H:20]2[CH2:21][CH2:22][C@H:23]([CH2:26][OH:27])[CH2:24][CH2:25]2)=[C:16]([F:28])[C:15]=1[F:29])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 178444948HCID 178444948, compound

Product 1

HCID 178444949HCID 178444949, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1.1 g) was suspended in THF (200 ml). trans-4-(4-Hexyloxy-2,3-difluorophenyl)-cyclohexanecarboaldehyde (s-15) (15.8 g) was added dropwise to the suspension in the temperature range of −20° C. to −10° C., and the stirring was continued in this temperature range for 2 hours. After the completion of the reaction had been confirmed by means of GC analysis, ethyl acetate and then a saturated aqueous solution of ammonia were added to the reaction mixture under ice-cooling and deposits were removed by filtration through Celite. The filtrate was extracted with ethyl acetate. The combined organic phase was washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by recrystallization from heptane to give trans-4-(4-hexyloxy-2,3-difluorophenyl)-hydroxymethylcyclohexane (s-16) (4.7 g). The yield based on the compound (s-15) was 29.6%.

Workup

  1. temperaturecooling
  2. customdeposits were removed by filtration through Celite
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washThe combined organic phase was washed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by recrystallization from heptane

Sources & evidence

ORD record
ord-3225331708864e46a77d4d3514b3f689
Source dataset
uspto-grants-2013_05
Patent number
US08435422B2

Reaction notes

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