tert-Butyl carbazate → methyl 5-(N'-tert-butoxycarbonylhydrazino)-5-(4-fluorophenyl)pentanoate

HRID 1009370Notes

Reaction equation

HRID 1009370 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.[C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])[NH:18][NH2:19].[H][H]>CC(O)C.[Pt]=O>[C:22]([O:21][C:17]([NH:18][NH:19][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 70091tert-Butyl carbazateHCID 21763150Methyl 5-(4-fluorophenyl)-5-oxopentanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 67067136methyl 5-(N'-tert-butoxycarbonylhydrazino)-5-(4-fluorophenyl)pentanoate

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 3776IsopropanolSolvent

Procedure

A solution of methyl 5-(4-fluorophenyl)-5-oxopentanoate (CAS No. 149437-67-2, 116 mg) and tert-butyl carbazate (73 mg) in 2-propanol (3 mL) was heated under reflux for six hours. The reaction solution was left to cool to room temperature, and then platinum oxide (10 mg) was added to the reaction solution. The reaction solution was stirred at room temperature in an hydrogen atmosphere at 3.5 atm for eight hours. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=9:1->heptane:ethyl acetate=1:1) to obtain 81 mg of the title compound. The property value of the compound is as follows.

Workup

  1. temperatureunder reflux for six hours
  2. waitThe reaction solution was left
  3. filtrationThe reaction solution was filtered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=9:1->heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-e02603147d2d472f928882358dea0065
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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