Hydrochloric Acid → 3-Hydroxyazetidine-3-carboxylic acid hydrochloride

HRID 2049994Notes

Reaction equation

HRID 2049994 reaction equation
C([N:14]1[CH2:17][C:16]([OH:21])([C:18]([OH:20])=[O:19])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[ClH:22]>O1CCOCC1.[Pd]>[ClH:22].[OH:21][C:16]1([C:18]([OH:20])=[O:19])[CH2:17][NH:14][CH2:15]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 203431191-Benzhydryl-3-hydroxy-azetidine-3-carboxylic acid

Product 1

HCID 670516543-Hydroxyazetidine-3-carboxylic acid hydrochlorideYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2.383 g (8.4 mmoles) of crude 1-benzhydryl-3-hydroxyazetidine-3-carboxylic acid in 64 ml of 50% aqueous dioxane is added 2.1 ml of concentrated hydrochloric acid, and the mixture is catalytically hydrogenated for 32 hours in the presence of 924 mg of 10% palladium-charcoal under hydrogen pressure of 5 kg/cm2. The catalyst is filtered off and washed with an aqueous dioxane. The combined filtrate and washings are evaporated under reduced pressure during which the precipitating oily material is removed by washing with ether. The residue is washed with acetone and recrystallized from dimethylformamide-acetone to yield 1.051 g of 3-hydroxyazetidine-3-carboxylic acid hydrochloride as prisms in 82% yield.

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with an aqueous dioxane
  3. customThe combined filtrate and washings are evaporated under reduced pressure during which the precipitating oily material
  4. customis removed
  5. washby washing with ether
  6. washThe residue is washed with acetone
  7. customrecrystallized from dimethylformamide-acetone

Sources & evidence

ORD record
ord-ca64bcd6113649a4bfedbb6278bf4805
Source dataset
uspto-grants-1980_04
Patent number
US04199570

Reaction notes

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