Ammonia → HCID 67082406, compound

HRID 1943554Notes

Reaction equation

HRID 1943554 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([CH:12]1[CH2:17][CH2:16][C:15]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=2[F:33])([C:18]2(C=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11].[C:34](OCC)(=[O:36])C.N>C1COCC1>[OH:36][CH2:34][CH:21]1[CH2:22][CH2:23][CH:18]([C:15]2([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=3[F:33])[CH2:16][CH2:17][CH:12]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:13][CH2:14]2)[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 86652490HCID 86652490, compound

Product 1

HCID 67082406HCID 67082406, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (0.45 g) was suspended in THF (100 ml). The compound (40) (7.5 g) dissolved in THF (100 ml) was added dropwise to this suspension in the temperature range of −20° C. to −10° C., and the mixture was stirred in this temperature range for another 2 hours. After the termination of the reaction had been confirmed by GC analysis, ethyl acetate and a saturated aqueous solution of ammonia were sequentially added to the reaction mixture under ice-cooling, and deposits were removed by filtration through Celite. The filtrate was extracted in ethyl acetate. The organic phase obtained was washed sequentially with water and saturated brine, and then dried over anhydrous magnesium sulfate. Then, the product was purified by means of recrystallization from heptane, dried and concentrated under reduced pressure, giving 7.4 g of 4-hydroxymethyl-[4-pentyl-(2,3-difluorophenyl)cyclohexyl]-cyclohexane (41). The yield based on the compound (40) was 98.1%.

Workup

  1. additionwas added dropwise to this suspension in the temperature range of −20° C. to −10° C.
  2. temperaturecooling
  3. customdeposits were removed by filtration through Celite
  4. extractionThe filtrate was extracted in ethyl acetate
  5. customThe organic phase obtained
  6. washwas washed sequentially with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThen, the product was purified by means of recrystallization from heptane
  9. customdried
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-38bebbbc4c1d404fa06d671a7ea8f121
Source dataset
uspto-grants-2013_03
Patent number
US08394294B2

Reaction notes

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