Acetonitrile → HCID 70981157, compound

HRID 1475441Notes

Reaction equation

HRID 1475441 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][F:15])[NH:11][CH2:10][C@H:9]1[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].C(#N)C>O>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][F:15])[N:11]([CH2:24][C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH2:10][C@H:9]1[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 70981902HCID 70981902, compound

Product 1

HCID 70981157HCID 70981157, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of (2R,5R)-5-fluoromethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (0.371 g, 1.27 mmol), potassium carbonate (0.70 g, 5.1 mmol), benzyl bromoacetate (0.38 g, 1.65 mmol) and acetonitrile (10 mL) was stirred at 20° C. for 18 h. Mixture was poured into water (50 mL) and extracted with DCM (3×30 mL). Combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give an oil. Chromatography (SiO2; gradient elution with 0-100% Et2O in 40-60 petroleum ether) gave the title compound (0.424 g, 87%) as an oil. MS [M+H]+=381.

Workup

  1. extractionextracted with DCM (3×30 mL)
  2. dry with materialCombined organic extracts were dried (Na2SO4)
  3. customevaporated in vacuo
  4. customto give an oil
  5. washChromatography (SiO2; gradient elution with 0-100% Et2O in 40-60 petroleum ether)

Sources & evidence

ORD record
ord-f76fcf1d37224d9db2a420bcfc081c22
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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