HCID 19705533, compound → HCID 19705481, compound

HRID 727572Notes

Reaction equation

HRID 727572 reaction equation
[N:1]([CH:4]([C:12]1([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]1=[O:25])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])=[N+]=[N-]>[Pd].CCO>[NH2:1][CH:4]([C:12]1([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]1=[O:25])[C:5]([O:7][C:8]([CH3:9])([CH3:11])[CH3:10])=[O:6]

Participants

4

Reactant 1

HCID 19705533HCID 19705533, compound

Product 1

HCID 19705481HCID 19705481, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl α-azido-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (159 mg, 0.397 mmol), palladium on carbon (10%, 40 mg) and EtOH (2.0 mL) is hydrogenated overnight at 30 psi. The mixture is filtered and concentrated to give 145 mg (97%) of the title compound as an oil:

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6bb8fe20e64b444595ad2809a0486b1f
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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