2,4-Azetidinedicarboxylic acid, 1-(phenylmethyl)-, dimethyl ester, (2R,4S)-rel- → HCID 14654395, compound

HRID 1708866Notes

Reaction equation

HRID 1708866 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:8][C@@H:7]([C:9]([O:11][CH3:12])=[O:10])[N:6]1CC1C=CC=CC=1)=[O:4].[H][H]>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]([C@H:5]1[CH2:8][C@@H:7]([C:9]([O:11][CH3:12])=[O:10])[NH:6]1)=[O:4]

Participants

5

Reactant 2

HCID 146543812,4-Azetidinedicarboxylic acid, 1-(phenylmethyl)-, dimethyl ester, (2R,4S)-rel-HCID 178418361HCID 178418361, compound

Product 1

HCID 14654395HCID 14654395, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

79 mg (0.3 mmol) of cis-N-benzylazetidine-2,4-dicarboxylic acid dimethyl ester and 25 mg of Pd(OH)2 (20% on C, 31% H2O, Aldrich) in 10 ml of methanol are hydrogenated under 3 atm of hydrogen in a Parr shaker for 6 hours. The catalyst is filtered off and thoroughly washed, the solution evaporated, and the residue filtered over a short column to yield 23.4 mg (45%) of cis-azetidine-2,4-dicarboxylic acid dimethyl ester. 1H NMR (CDCl3): δ4.27 (dd, 2H, J=6.5, 8.5), 3.76 (s, 6H), 2.95 (dt, 1H, J=8.5 (t), 12 (d)), 2.60 (dt, 1H, J=6.5 (t), 12 (d)). IR (neat): 3345, 2955, 1740, 1437, 1231, 1042 cm-1. Mass spectrum: m/z 173 (7%), 114 (100), 82 (44), 59 (14), 55 (32), 54 (98). Calcd. for C7H11NO4 : 173.0688, found: 173.0688.

Workup

  1. filtrationThe catalyst is filtered off
  2. washthoroughly washed
  3. customthe solution evaporated
  4. filtrationthe residue filtered over a short column

Sources & evidence

ORD record
ord-86a8a842578343b8b02e9d94f5563cd2
Source dataset
uspto-grants-1990_08
Patent number
US04946839

Reaction notes

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