Ethanolamine → trans-1-Benzyl-4-hydroxy-3-(2-hydroxyethylamino)pyrrolidine

HRID 981076Notes

Reaction equation

HRID 981076 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[CH:10]([O:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:14][CH2:15][CH2:16][OH:17]>O>[CH2:1]([N:8]1[CH2:9][C@@H:10]([OH:11])[C@H:12]([NH:14][CH2:15][CH2:16][OH:17])[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexane

Product 1

HCID 15069972trans-1-Benzyl-4-hydroxy-3-(2-hydroxyethylamino)pyrrolidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

40 g (0.22 mol) of 3-benzyl-6-oxa-3-azabicyclo[3.1.0]hexane are heated under reflux with 42 g (0.68 mol) of 2-aminoethanol in 450 ml of water overnight. The solution is extracted once with tert.-butyl methyl ether and the aqueous phase is concentrated. The residue is distilled.

Workup

  1. extractionThe solution is extracted once with tert.-butyl methyl ether
  2. concentrationthe aqueous phase is concentrated
  3. distillationThe residue is distilled

Sources & evidence

ORD record
ord-565945edfc5a4a09a36d4ea6fff3e4db
Source dataset
uspto-grants-1991_02
Patent number
US04990517

Reaction notes

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