Epibromohydrin → HCID 86728089, compound

HRID 2202644Notes

Reaction equation

HRID 2202644 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[H-].[Na+].Br[CH2:18][CH:19]1[CH2:21][O:20]1>C1COCC1>[O:20]1[CH2:21][CH:19]1[CH2:18][N:7]1[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3][C:2]1=[O:1]

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 86728089HCID 86728089, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

tert-butyl 3-oxopiperazine-1-carboxylate (400 mg, 2 mmol) was dissolved in THF (20 mL) and cooled to 0° C. NaH (72 mg, 3 mmol) was added to the solution followed by 2-(bromomethyl)oxirane (326 mg, 2.4 mmol), and the resulting mixture was stirred at 0° C. for 16 h. The reaction mixture was quenched by addition of ice water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate and concentrated. The crude product was used without further purification. (400 mg, yield 78.1%).

Workup

  1. customThe reaction mixture was quenched by addition of ice water
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-c2534c47f8624716b1910bb31c31594d
Source dataset
uspto-grants-2016_06
Patent number
US09365555B2

Reaction notes

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