tert-Butyl carbazate → HCID 66777612, compound

HRID 406342Notes

Reaction equation

HRID 406342 reaction equation
O=[C:2]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1)[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[C:21]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])(=[O:24])[NH:22][NH2:23].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.C(O)(=O)C.C(OCC)C>[C:26]([O:25][C:21]([NH:22][NH:23][CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1)[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

8

Reactant 4

HCID 70091tert-Butyl carbazateHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride2×HCID 24727515Ethyl 5-oxo-5-[3-(trifluoromethyl)phenyl]pentanoate

Product 1

HCID 66777612HCID 66777612, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-oxo-5-(3-trifluoromethylphenyl)pentanoate (CAS No. 898777-75-8, 330 mg) and tert-butyl carbazate (227 mg) were dissolved in a mixed solvent of THF (6 mL) and acetic acid (3 mL). After stirring at room temperature for 25 minutes, sodium cyanoborohydride (108 mg) was added. After further one hour and 30 minutes, sodium cyanoborohydride (108 mg) was added and the mixture was stirred at room temperature for one hour. A saturated sodium bicarbonate solution and diethyl ether 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 (324 mg). The property values of the compound are as follows.

Workup

  1. waitAfter further one hour
  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-d69413fe023f46948615c7f96f1bddd4
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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