Bromine → Ethyl 8-(benzyloxy)-6-bromo-2-methyl-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]-pyrazine-7-carboxylate

HRID 2114851Notes

Reaction equation

HRID 2114851 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:11][N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[Br:30]Br>ClCCl>[CH2:1]([O:8][C:9]1[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:11]([Br:30])[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[C:13]=12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 68864077Ethyl 1,2,3,4-tetrahydro-2-methyl-1-oxo-8-(phenylmethoxy)pyrrolo[1,2-a]pyrazine-7-carboxylate

Product 1

HCID 68866169Ethyl 8-(benzyloxy)-6-bromo-2-methyl-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]-pyrazine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of ethyl 8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]-pyrazine-7-carboxylate (5.0 g, 15.2 mmol; Example 32, step 5) and sodium bicarbonate (19.2 g, 228 mmol) in dichloromethane (150 mL) at 0° C., a solution of bromine in dichloromethane (0.5 M, 32 mL, 16 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 2 h, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluted with a hexane-ethyl acetate gradient to provide the titled product.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under vacuum
  3. washeluted with a hexane-ethyl acetate gradient

Sources & evidence

ORD record
ord-1c808dd8afb24829905c73584bfded74
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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