Methyl bromoacetate → Methyl N-(2,2-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)glycinate

HRID 5769Notes

Reaction equation

HRID 5769 reaction equation
[NH2:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1([CH3:13])[CH3:12].[CH3:14][O:15][C:16](=[O:19])[CH2:17]Br>C(OCC)C>[CH3:14][O:15][C:16](=[O:19])[CH2:17][NH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 197941112,2-Dimethyl-1,2,3,4-tetrahydronaphthalen-1-amine

Product 1

HCID 19794110Methyl N-(2,2-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)glycinate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

65.2 g of 1-amino-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene are solved in 250 ml of diethyl ether. To this solution is dropwise added a solution of 28.5 g of bromoacetic acid methyl ester in 150 ml of diethyl ether. The mixture is stirred at room temperature for 70 hours. The precipitate is separated and the solution is concentrated to dryness, yielding N-(2,2-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl) glycine methyl ester quantitatively.

Workup

  1. customThe precipitate is separated
  2. concentrationthe solution is concentrated to dryness

Sources & evidence

ORD record
ord-803d1399dfd7461184d0632b8742a4e8
Source dataset
uspto-grants-1993_09
Patent number
US05246915

Reaction notes

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