HCID 54342562, compound → HCID 54072887, compound

HRID 399519Notes

Reaction equation

HRID 399519 reaction equation
[C:1]([O:5][C:6](=[O:21])[C@@H:7]1[CH2:11][C@@H:10]([C:12]#[N:13])[CH2:9][N:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:21])[C@@H:7]1[CH2:11][C@H:10]([CH2:12][NH2:13])[CH2:9][N:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 54342562HCID 54342562, compound

Product 1

HCID 54072887HCID 54072887, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution (4R)-1-(tert-butyloxycarbonyl)-4-cyano-L-proline tert-butyl ester (220 mg, 0.742 mmol) in 90% ethanol (11 mL) was hydrogenated in the presence of 10% palladium-on-charcoal (100 mg) at 450 psi for 18 hours. The catalyst was removed by filtration through Celite, the filter washed with methanol, 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 164 mg (74%).

Workup

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

Sources & evidence

ORD record
ord-ef1247e8e35b45c2bb8f40c5aeb3b196
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

Loading…