Acetic Acid → HCID 103563890, compound

HRID 2206253Notes

Reaction equation

HRID 2206253 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:6][CH2:5][CH2:4][C:3]1=[N:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C(O)(=O)C.C([BH3-])#N.[Na+].Cl[O-].[Na+]>C1COCC1>[CH3:1][C:2]1([CH3:16])[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 23665760Sodium HypochloriteHCID 117988010HCID 117988010, compound

Product 1

HCID 103563890HCID 103563890, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of tert-butyl 2-(2,2-dimethylcyclopentylidene)hydrazinecarboxylate (4.6 g) and acetic acid (9.4 g) in THF (80 mL) was added sodium cyanoborohydride (5.1 g) at room temperature. The reaction mixture was stirred at 85° C. for 10 hr, aqueous sodium hypochlorite solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to give the title compound (2.4 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-f10e0a5b0c7b48eab27865d75326cda1
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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