Water → 1-benzylazetidine-3,3-dicarboxylic Acid

HRID 868183

Reaction equation

HRID 868183 reaction equation
BrBr.[CH2:3]([N:10]1[CH2:13][C:12]([CH2:16][OH:17])([CH2:14][OH:15])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-:18].[Na+].[OH2:20]>S([O-])([O-])(=O)=O.[Ni+2]>[CH2:3]([N:10]1[CH2:13][C:12]([C:14]([OH:20])=[O:15])([C:16]([OH:18])=[O:17])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24408BromineHCID 20164320[1-Benzyl-3-(hydroxymethyl)azetidin-3-YL]methanol

Product 1

HCID 113108851-benzylazetidine-3,3-dicarboxylic Acid

Reagents, catalysts & solvents 1

HCID 24586Nickel SulfateCatalyst

Procedure

Bromine (10.6 g) was slowly added at 20° C. over 8 hours to a mixture of N-benzyl-3,3-bis(hydroxymethyl)azetidine (2.1 g) in water (50 ml) containing sodium hydroxide (9.3 g) and nickel chloride 6.0 aq. (1.5 g). After stirring overnight, the green precipitate of nickel hydroxide was filtered off, and the filtrate evaporated to dryness. The residue was boiled in ethanol, and the insoluble material (desired product as sodium salt and sodium bromide) separated and worked up to yield the N-benzyl-azetidine-3,3-dicarboxylic acid.

Workup

  1. filtrationthe green precipitate of nickel hydroxide was filtered off
  2. customthe filtrate evaporated to dryness
  3. customthe insoluble material (desired product as sodium salt and sodium bromide) separated

Sources & evidence

ORD record
ord-838be3ff0e684522a9c780bbcef962f4
Source dataset
uspto-grants-1988_10
Patent number
US04778577

Linked notes

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