Acetone Cyanohydrin → HCID 67359758, compound

HRID 1668377Notes

Reaction equation

HRID 1668377 reaction equation
[C:1]([N:4]([CH3:21])[N:5]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19]O)=[CH:15][CH:14]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2].CC(C)(O)[C:24]#[N:25].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>C1COCC1>[C:1]([N:4]([CH3:21])[N:5]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:24]#[N:25])=[CH:15][CH:14]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 59239817HCID 59239817, compound

Product 1

HCID 67359758HCID 67359758, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 2-acetyl-1-[4-(hydroxymethyl)phenyl]-2-methylhydrazinecarboxylate (1.27 g), acetone cyanohydrin (550 mg) and 1,1′-(azodicarbonyl)dipiperidine (1.63 g) were dissolved in THF (60 ml), and tributylphosphine (1.31 g) was added at 0° C. The obtained mixture was stirred at room temperature for 18 hr, and concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was washed with water and then saturated brine. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 (volume ratio)→1:1 (volume ratio)), and further recrystallized from ethyl acetate-hexane to give the title compound (910 mg) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. washthe mixture was washed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane
  7. customethyl acetate=9:1 (volume ratio)→1:1 (volume ratio)), and further recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-3d2565d72f254dad96f2de85f03bc8f7
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

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