HCID 67640328, compound → HCID 67640683, compound

HRID 399516Notes

Reaction equation

HRID 399516 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 67640328HCID 67640328, compound

Product 1

HCID 67640683HCID 67640683, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution (4S)-1-(tert-butyloxycarbonyl)-4-cyano-L-proline tert-butyl ester (470 mg, 1.59 mmol) in 90% ethanol (22 mL) was hydrogenated in the presence of 10% palladium-on-charcoal (225 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 284 mg (60%). 400 MHz 1H NMR (CD3OD): δ1.41-1.48 (3s, 18H); 1.58 (m, 1H); 2.28 (m, 1H); 2.48 (m, 1H); 2.66 (m, 2H); 3.05 (dd, 1H); 3.71 (dd, 1H); 4.12 (m, 1H).

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-aeb7fd57321348fdb99c27347f87fcdb
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

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