1-tert-Butyl 2-methyl (2S,4R)-4-cyanopyrrolidine-1,2-dicarboxylate → 1-tert-Butyl 2-methyl (2S,4R)-4-(aminomethyl)pyrrolidine-1,2-dicarboxylate

HRID 399535Notes

Reaction equation

HRID 399535 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@@H:4]1[CH2:8][C@@H:7]([C:9]#[N:10])[CH2:6][N:5]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:18])[C@@H:4]1[CH2:8][C@H:7]([CH2:9][NH2:10])[CH2:6][N:5]1[C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12]

Participants

4

Reactant 1

HCID 179989661-tert-Butyl 2-methyl (2S,4R)-4-cyanopyrrolidine-1,2-dicarboxylate

Product 1

HCID 574157221-tert-Butyl 2-methyl (2S,4R)-4-(aminomethyl)pyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution (4R)-1-(tert-butyloxycarbonyl)-4-cyano-L-proline methyl ester (204 mg, 0.802 mmol) in 90% ethanol (12 mL) was hydrogenated in the presence of 10% palladium-on-charcoal (60 mg) at 450 psi for 24 hours. The catalyst was removed by filtration through Celite, the filter washed with ethanol, and the combined filtrate and washings evaporated. Purification was achieved by flash silica gel chromatography eluting with 95:5:0.5 chloroform-methanol-ammonia; yield 66 mg (32%).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. washthe filter washed with ethanol
  3. customthe combined filtrate and washings evaporated
  4. customPurification
  5. washeluting with 95:5:0.5 chloroform-methanol-ammonia

Sources & evidence

ORD record
ord-36b06b6aaae147108ff2cb721101ac44
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

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