Ethyl bromoacetate → Ethyl N-(2,3-dihydro-1H-inden-5-yl)glycinate

HRID 620224Notes

Reaction equation

HRID 620224 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.C(N(CC)CC)C.Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[CH2:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 90496Indan-5-amine

Product 1

HCID 15614976Ethyl N-(2,3-dihydro-1H-inden-5-yl)glycinate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-aminoindan (15.0 g, 0.1128 mol) and triethylamine (11.92 g, 0.1184 mol) in 200 ml ethanol was added dropwise ethyl bromoacetate (18.83 g, 0.1128 mol). After the addition was complete the mixture was stirred at room temperature for 24 h and concentrated in vacuo. The residue was dissolved in ether, washed with H2O (4×300 ml), brine and dried (MgSO4). Concentration of the volatiles in vacuo provided a crystalline material which was recrystallized from petroleum ether; b.p. 30°-60° C., m.p. 49° C.

Workup

  1. additionAfter the addition
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with H2O (4×300 ml), brine
  5. dry with materialdried (MgSO4)
  6. customConcentration of the volatiles in vacuo provided a crystalline material which
  7. customwas recrystallized from petroleum ether

Sources & evidence

ORD record
ord-2764da5df8924709907da4025932ca6e
Source dataset
uspto-grants-1989_04
Patent number
US04820729

Reaction notes

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