tert-Butyl carbazate → 1,1-Dimethylethyl 2-[4-(methoxycarbonyl)-4-[4-(trifluoromethyl)phenyl]cyclohexyl]hydrazinecarboxylate

HRID 406346Notes

Reaction equation

HRID 406346 reaction equation
O=[C:2]1[CH2:7][CH2:6][C:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1.[C:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:25])[NH:23][NH2:24].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.C(O)(=O)C.C(OCC)C>[C:27]([O:26][C:22]([NH:23][NH:24][CH:2]1[CH2:7][CH2:6][C:5]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1)=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

8

Reactant 4

HCID 70091tert-Butyl carbazateHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride2×HCID 66618878HCID 66618878, compound

Product 1

HCID 666188011,1-Dimethylethyl 2-[4-(methoxycarbonyl)-4-[4-(trifluoromethyl)phenyl]cyclohexyl]hydrazinecarboxylateYield 53.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-oxo-1-(4-trifluoromethylphenyl)cyclohexanecarboxylate (100 mg) and tert-butyl carbazate (66 mg) were dissolved in a mixed solvent of THF (6 mL) and acetic acid (3 mL). After stirring at room temperature for 50 minutes, sodium cyanoborohydride (31.4 mg) was added. After further two hours, sodium cyanoborohydride (31.4 mg) was added and the mixture was stirred at room temperature for one hour. Diethyl ether and a saturated sodium bicarbonate solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with a saturated sodium bicarbonate solution and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (74.5 mg). The property values of the compound are as follows.

Workup

  1. waitAfter further two hours
  2. stirringthe mixture was stirred at room temperature for one hour
  3. customthe organic layer was separated
  4. washThe resulting organic layer was washed with a saturated sodium bicarbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe drying agent was separated by filtration
  7. concentrationthe organic layer was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d6768d1e1b2f499eb08c0034609bebba
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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