HCID 15431799, compound → L-cis-Pyrrolidine-2,4-dicarboxylic acid

HRID 1586102Notes

Reaction equation

HRID 1586102 reaction equation
C([N:11]1[CH2:18][C@@H:17]([C:19]([OH:21])=[O:20])[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])(OCC1C=CC=CC=1)=O>CO.[Pd]>[C:19]([C@@H:17]1[CH2:18][NH:11][C@H:12]([C:13]([OH:15])=[O:14])[CH2:16]1)([OH:21])=[O:20]

Participants

4

Reactant 1

HCID 15431799HCID 15431799, compound

Product 1

HCID 1515194L-cis-Pyrrolidine-2,4-dicarboxylic acidYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-CBZ-cis-4-carboxy-L-proline (0.455 g, 1.55 mmol) was dissolved in methanol (37 mL) and transferred into a Parr shaker bottle. After adding 10% Pd-C (0.080 g), the mixture was shaken under an atmosphere of hydrogen at 48-50 psi for 0.5 h on the Parr apparatus. The catalyst was removed by filtration through Celite. The filter-cake was washed with water and the combined filtrate and washings were concentrated in vacuo to yield a white solid, which was recrystallized from H2O-ethanol-acetone to yield 0.206 g (84%) of 4 as colorless prisms: mp 225°-226° C.; [α]25D -40° (c 1.02, H2O); 1H NMR (250 MHz, D2O) δ 4.25 (dd, J=8.6, 7.4 Hz, 1 H, H-2), 3.72 (dd, J=12.0, 6.7 Hz, 1 H, H-5), 3.57 (dd, J=12.0, 8.0 Hz, 1 H, H-5), 3.38 (m, 1H, H-4), 2.71 (app dt, J=13.7, 8.6 Hz, 1 H, H-3), 2.35 (app overlapping dt, J=13.7, 7.4 Hz, 1 H,H-3); 13C NMR (75.5 MHz, D2O) δ 178.75, 176.25, 63.87, 50.16, 45.43, 34.78; IR (KBr) 3600-2200 (broad), 3080, 1690, 1560, 1340, 1230 cm-1 ; MS (CI, 70 eV, methane) m/e 160 (MH+, 14), 114 (100). Anal. Calcd for C6H9NO4 : C, 45.28; H, 5.70; N, 8.80. Found: C, 45.31; H, 5.51; N, 8.75.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. washThe filter-cake was washed with water
  3. concentrationthe combined filtrate and washings were concentrated in vacuo
  4. customto yield a white solid, which
  5. customwas recrystallized from H2O-ethanol-acetone

Sources & evidence

ORD record
ord-9bdb920d4459468e9710222db6f2edf1
Source dataset
uspto-grants-1999_08
Patent number
US05942537

Reaction notes

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