HCID 67831590, compound → 2,4-Azetidinedicarboxylic acid, mono(1,1-dimethylethyl) ester, cis-

HRID 981029Notes

Reaction equation

HRID 981029 reaction equation
[C:1]([O:5][C:6]([C@H:8]1[N:11](CC2C=CC=CC=2)[C@@H:10]([C:19]([O:21]CC2C=CC=CC=2)=[O:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:5][C:6]([C@H:8]1[CH2:9][C@@H:10]([C:19]([OH:21])=[O:20])[NH:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 67831590HCID 67831590, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 146544092,4-Azetidinedicarboxylic acid, mono(1,1-dimethylethyl) ester, cis-Yield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

267 mg (0.7 mmol) of stereochemically pure transor cis-N-benzylazetidine-2,4-dicarboxylic acid benzyl t-butyl ester, 50mg of 10% Pd/C, and 20 ml of methanol are hydrogenated under 3 atm of hydrogen in a Parr shaker for 4 hours. The catalyst is filtered off and thoroughly washed, and the solution evaporated to dryness and dried in vacuo to afford as off-white solids the trans- or cis-azetidine-2,4-dicarboxylic acid mono-t-butyl ester.

Workup

  1. filtrationThe catalyst is filtered off
  2. washthoroughly washed
  3. customthe solution evaporated to dryness
  4. customdried in vacuo

Sources & evidence

ORD record
ord-afaae5fc9f7d434c8312c4b985dcb563
Source dataset
uspto-grants-1991_02
Patent number
US04990504

Reaction notes

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