Sodium hydride → 3-[[1-[3-(Trifluoromethyl)phenyl]hydrazino]carbonyl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

HRID 2113500Notes

Reaction equation

HRID 2113500 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH:13]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)=[O:15])[CH:12]2[CH2:27][CH:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])[CH3:3].[H-].[Na+].C1(P(C2C=CC=CC=2)(O[NH2:39])=O)C=CC=CC=1>O1CCCC1>[CH3:4][C:2]([O:5][C:6]([N:8]1[CH:13]([C:14]([N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:26])[F:24])[CH:18]=2)[NH2:39])=[O:15])[CH:12]2[CH2:27][CH:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10955453O-(Diphenylphosphinyl)hydroxylamineHCID 235994073-[[[3-(Trifluoromethyl)phenyl]amino]carbonyl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Product 1

HCID 235994083-[[1-[3-(Trifluoromethyl)phenyl]hydrazino]carbonyl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 18A (308 mg, 0.8 mmol, 1 eq) was dissolved in 15 mL of tetrahydrofuran. Sodium hydride (60% in oil, 38 mg, 0.96 mmol, 1.2 eq) was added, and the mixture was stirred at rt for 15 min. O-Diphenylphosphinylhydroxylamine (224 mg, 0.96 mmol, 1.2 eq) was then added, and the reaction was stirred at rt for 1 h. LC analysis indicated that the starting material had been consumed. Water was added, and the reaction was extracted with CH2Cl2. The combined organic extracts were dried and concentrated in vacuo to provide Compound 18B as a semi-solid in quantitative yield. The compound was used without further purification. LC: R.T.=3.39 min (retention time) (YMC Combiscreen ODS-A S5 column eluting with 10-90% aqueous methanol over a 4 minute gradient.)

Workup

  1. stirringthe reaction was stirred at rt for 1 h
  2. customhad been consumed
  3. additionWater was added
  4. extractionthe reaction was extracted with CH2Cl2
  5. customThe combined organic extracts were dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47c0ed2cf8e54c73bb1630226d151013
Source dataset
uspto-grants-2008_10
Patent number
US07432267B2

Reaction notes

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