Formaldehyde → 1-Methyl-3-hydroxyazetidine-3-carboxylic acid

HRID 2049995Notes

Reaction equation

HRID 2049995 reaction equation
Cl.[OH:2][C:3]1([C:7]([OH:9])=[O:8])[CH2:6][NH:5][CH2:4]1.[CH2:10]=O>O.O.[Pt]=O>[CH3:10][N:5]1[CH2:6][C:3]([OH:2])([C:7]([OH:9])=[O:8])[CH2:4]1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 670516543-Hydroxyazetidine-3-carboxylic acid hydrochloride

Product 1

HCID 203431201-Methyl-3-hydroxyazetidine-3-carboxylic acidYield 74.9%

Reagents, catalysts & solvents 2

HCID 86587499Platinum oxide monohydrateCatalystHCID 962WaterSolvent

Procedure

To a solution of 500 mg (3.26 mmoles) of 3-hydroxyazetidine-3-carboxylic acid hydrochloride in 15 ml of water are added 1.06 ml of 37% formalin and 250 mg of platinum oxide monohydrate, and the mixture is kept at ambient temperature under atmospheric pressure for 46 hours. The catalyst is filtered off and washed with water. The combined filtrate and washings are evaporated under reduced pressure. The residue (0.79 g) is dissolved in 10 ml of water, adsorbed on 30 ml of Amberlite IR-120 B (H+), and eluted with 100 ml of 2 N aqueous ammonium hydroxide solution. The eluate is evaporated under reduced pressure. The residue (431 mg) is crystallized from water-acetone to yield 1-methyl-3-hydroxyazetidine-3-carboxylic acid as prisms.

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with water
  3. customThe combined filtrate and washings are evaporated under reduced pressure
  4. dissolutionThe residue (0.79 g) is dissolved in 10 ml of water
  5. washeluted with 100 ml of 2 N aqueous ammonium hydroxide solution
  6. customThe eluate is evaporated under reduced pressure
  7. customThe residue (431 mg) is crystallized from water-acetone

Sources & evidence

ORD record
ord-6429c318e65548dd8dbde497d5b46bbe
Source dataset
uspto-grants-1980_04
Patent number
US04199570

Reaction notes

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