Ethyl 3-(hydroxymethyl)-4-(methylamino)pyrrolidine-1-carboxylate → (4-(Methylamino)pyrrolidin-3-yl)methanol

HRID 36689Notes

Reaction equation

HRID 36689 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][N:6](C(OCC)=O)[CH2:5][CH:4]1[NH:13][CH3:14]>O>[OH:1][CH2:2][CH:3]1[CH2:7][NH:6][CH2:5][CH:4]1[NH:13][CH3:14]

Participants

3

Reactant 1

HCID 15070021Ethyl 3-(hydroxymethyl)-4-(methylamino)pyrrolidine-1-carboxylate

Product 1

HCID 15070024(4-(Methylamino)pyrrolidin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

34 g (0.168 mol) of ethyl 4-hydroxymethyl-3-methylaminopyrrolidine-1-carboxylate are heated under reflux with 100 g of Ba(OH)2.8H2O in 400 ml of water overnight. The BaCO3 is filtered off with suction, the filtrate is concentrated and the residue is boiled up ten times with 100 ml of dioxane each time. The dioxane solutions are filtered, the filtrate is concentrated and the residue is distilled.

Workup

  1. filtrationThe BaCO3 is filtered off with suction
  2. concentrationthe filtrate is concentrated
  3. filtrationThe dioxane solutions are filtered
  4. concentrationthe filtrate is concentrated
  5. distillationthe residue is distilled

Sources & evidence

ORD record
ord-86770ff2bc704ac38d0ea5db59a975f1
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Reaction notes

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