Water → HCID 57137078, compound

HRID 1680502Notes

Reaction equation

HRID 1680502 reaction equation
[CH2:1]1[CH:6]2[C:7]3[C:12]([C:13](=[O:14])[N:5]2[CH2:4][CH2:3][NH:2]1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[H-].[Na+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].O>C1C=CC=CC=1>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][CH:1]1[CH:6]2[C:7]3[C:12]([C:13](=[O:14])[N:5]2[CH2:4][CH2:3][NH:2]1)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 12901777HCID 12901777, compound

Product 1

HCID 57137078HCID 57137078, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

A solution of 1,2,3,4,6,10b-hexahydropyrazino[2,1-a]isoindol-6-one (described in Example 8, 7.5 g, 0.04 mol) in 150 ml of benzene is added to sodium hydride (1.7 g of a 50% dispersion in mineral oil, 0.036 mol) in 200 ml of benzene and stirred at room temperature for 30 min. A solution of ethyl bromoacetate (8.8 g, 0.044 mol) in 150 ml of benzene is added and the reaction is refluxed with stirring for 3 hr and cooled. Water is cautiously added and the benzene layer is separated, washed with water, dried, and evaporated. The residue is chromatographed on silica gel using 50% acetone in benzene and the eluates are evaporated to give 6-oxo-1,2,3,4,6,10b-hexahydropyrazino[2,1-a]isoindole-1-acetic acid ethyl ester (5.5 g), nmr (CDCl3) δ1.3(t), 2.4-2.6(m), 2.8-3.5(m), 4.2(q), 4.6(m) and 7.3-7.7(m).

Workup

  1. temperaturethe reaction is refluxed
  2. stirringwith stirring for 3 hr
  3. temperaturecooled
  4. customthe benzene layer is separated
  5. washwashed with water
  6. customdried
  7. customevaporated
  8. customThe residue is chromatographed on silica gel using 50% acetone in benzene
  9. customthe eluates are evaporated

Sources & evidence

ORD record
ord-830be968aeac4b89b06ddcc30b1b74a3
Source dataset
uspto-grants-1981_06
Patent number
US04273773

Reaction notes

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