Ethyl diazoacetate → HCID 57634640, compound

HRID 2109862Notes

Reaction equation

HRID 2109862 reaction equation
[C:1]([N:4]1[CH:9]=[CH:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:6](=[O:18])[CH2:5]1)(=[O:3])[CH3:2].[N+](=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N-]>C1(C)C=CC=CC=1.[Cu]>[C:1]([N:4]1[CH:9]2[CH:8]([CH:21]2[C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:6](=[O:18])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 57634629HCID 57634629, compound

Product 1

HCID 57634640HCID 57634640, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1140TolueneSolvent

Procedure

To a suspension of 4-acetyl-1-(4-fluorobenzyl)-3,4-dihydropyrazin-2(1H)-one (5.0 g, 20.0 mmol; Example 2, Step 3) and copper bronze (320 mg, 5.0 mmol) in anhydrous toluene (50 mL) under nitrogen at 120° C. (oil bath) was added ethyl diazoacetate (6.4 mL, 60.0 mmol) via a syringe pump at a speed of 2.5 mL/h. After 3 h, TLC (eluted with ethyl acetate) showed no starting material left. The reaction mixture was cooled to room temperature, filtered and concentrated. The residue was purified by column chromatography on silica gel using ethyl acetate and methanol as eluents to give both exo and endo diastereomers.

Workup

  1. washTLC (eluted with ethyl acetate)
  2. waitleft
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel
  6. customto give both exo and endo diastereomers

Sources & evidence

ORD record
ord-34ce5b0385e442979dfcfb37aa1f46f4
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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