tert-Butyl carbazate → HCID 118343059, compound

HRID 2202737Notes

Reaction equation

HRID 2202737 reaction equation
[CH3:1][C:2]1([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])[NH:16][NH2:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CC(O)=O>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][C:2]1([CH3:1])[CH2:7][CH2:6][CH:5]([NH:17][NH:16][C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:4][CH2:3]1)[CH3:14]

Participants

7

Reactant 4

HCID 70091tert-Butyl carbazateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 77230939HCID 77230939, compound

Product 1

HCID 118343059HCID 118343059, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

Ethyl 2-(1-methyl-4-oxocyclohexyl)acetate (1.5 g, 7.57 mmol) and tert-butyl carbazate (1.100 g, 8.32 mmol) were dissolved in chloroform (30 mL), and AcOH (1.0 mL) and NaBH(OAc)3 (5.65 g) were added under ice-cooling. The mixture was allowed to gradually return to room temperature, and the mixture was stirred for 4 h. The reaction mixture was poured into saturated aqueous NaHCO3 solution, and the mixture was extracted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:EtOAc, 100%-35%) to give tert-butyl 2-(4-(2-ethoxy-2-oxoethyl)-4-methylcyclohexyl)hydrazinecarboxylate (1.72 g, 5.47 mmol, 72.3% yield) as a mixture of isomers (colorless oil). LCMS=315.4 (M+H)+.

Workup

  1. temperaturecooling
  2. customto gradually return to room temperature
  3. extractionthe mixture was extracted with EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:EtOAc, 100%-35%)

Sources & evidence

ORD record
ord-5842549442db4ff6911bbc79c214e82c
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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