Tetrahydrofuran → HCID 86724969, compound

HRID 1847044Notes

Reaction equation

HRID 1847044 reaction equation
[N:1]([CH2:4][C@@H:5]1[CH2:9][N:8]([C:10]2[CH:11]=[CH:12][C:13]3[O:18][CH2:17][C:16](=[O:19])[NH:15][C:14]=3[CH:20]=2)[C:7](=[O:21])[CH2:6]1)=[N+]=[N-].O1CCCC1>CO.[Pd]>[NH2:1][CH2:4][C@@H:5]1[CH2:9][N:8]([C:10]2[CH:11]=[CH:12][C:13]3[O:18][CH2:17][C:16](=[O:19])[NH:15][C:14]=3[CH:20]=2)[C:7](=[O:21])[CH2:6]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 86724968HCID 86724968, compound

Product 1

HCID 86724969HCID 86724969, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-[(4S)-4-(azidomethyl)-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-one (430 mg, 1.50 mmol) in methanol (40 ml)/tetrahydrofuran (40 ml) was added 10% palladium on carbon catalyst (53% aqueous, 100 mg) at room temperature and the mixture was stirred at the same temperature for 2 hours under a hydrogen atmosphere. The catalyst was removed by filtration and the residue obtained by concentrating the filtrate was purified by silica gel column chromatography (NH silica gel, dichloromethane/methanol) to yield 336 mg (86%) of the title compound in the form of a light yellow amorphous solid.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe residue obtained
  3. concentrationby concentrating the filtrate
  4. customwas purified by silica gel column chromatography (NH silica gel, dichloromethane/methanol)

Sources & evidence

ORD record
ord-c93858e8155e4436ae63901a216e5cb2
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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