HCID 19705507, compound → HCID 19705458, compound

HRID 727567Notes

Reaction equation

HRID 727567 reaction equation
[N:1]([CH2:4][CH:5]([C:13]1([CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]1=[O:26])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[N+]=[N-]>[Pd].CCO>[NH2:1][CH2:4][CH:5]([C:13]1([CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]1=[O:26])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

4

Reactant 1

HCID 19705507HCID 19705507, compound

Product 1

HCID 19705458HCID 19705458, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl α-(1-azidomethyl)-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (648 mg, 1.56 mmol) and 10% palladium on carbon (163 mg) in EtOH (25 mL) is hydrogenated at 30 psi in a Parr flask for 16 hours. The mixture is filtered, rinsing the residual solids with MeOH and CH2 Cl2. The filtrate is concentrated and purified by silica gel chromatography (15 g SG; EtOAc, 15% MeOH/EtOAc) to provide 356 mg (57%) of the title compound as a partially crystalline solid:

Workup

  1. filtrationThe mixture is filtered
  2. washrinsing the residual solids with MeOH and CH2 Cl2
  3. concentrationThe filtrate is concentrated
  4. custompurified by silica gel chromatography (15 g SG; EtOAc, 15% MeOH/EtOAc)

Sources & evidence

ORD record
ord-31d212f9be3240f3b98cf1b04dd482d7
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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