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

HRID 981109Notes

Reaction equation

HRID 981109 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-bab319d9d25742f289722319af7d1b8d
Source dataset
uspto-grants-1991_02
Patent number
US04990517

Reaction notes

Loading…