HCID 86624151, compound → HCID 67270247, compound

HRID 602473Notes

Reaction equation

HRID 602473 reaction equation
[N:1]([C@@H:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:6]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:5]1)=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][C@@H:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[C@H:6]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:5]1

Participants

4

Reactant 1

HCID 86624151HCID 86624151, compound

Product 1

HCID 67270247HCID 67270247, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of tert-butyl (2R,4S)-4-azido-2-(3-ethoxy-3-oxopropyl)pyrrolidine-1-carboxylate (562 mg, 1.20 mmol, step 4 of Example 8) in ethanol (10 mL) was added 10 wt. % palladium on carbon (50 mg). The resulting mixture was stirred under hydrogen (4 atom) at room temperature for 3 h. The mixture was filtered through a pad of Celite and the filter cake was washed with ethanol. The combined filtrate was concentrated to give 352 mg (97%) of the title compound as a colorless oil.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washthe filter cake was washed with ethanol
  3. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-2619a3c5045947f59c8faf37621a68ab
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

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