6-[(4S)-4-(azidomethyl)-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-on → 6-[(4R)-4-(Aminomethyl)-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

HRID 1847047Notes

Reaction equation

HRID 1847047 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:14][CH2:15][C:16](=[O:20])[NH:17][C:18]=3[N:19]=2)[C:7](=[O:21])[CH2:6]1)=[N+]=[N-]>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:14][CH2:15][C:16](=[O:20])[NH:17][C:18]=3[N:19]=2)[C:7](=[O:21])[CH2:6]1

Participants

4

Reactant 1

HCID 867249746-[(4S)-4-(azidomethyl)-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-on

Product 1

HCID 867249736-[(4R)-4-(Aminomethyl)-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-oneYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-[(4S)-4-(azidomethyl)-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-on (688 mg, 2.39 mmol) in methanol (20 ml) was added 10% palladium on carbon catalyst (about 50% aqueous, 360 mg) at room temperature and the mixture was stirred at room temperature for 1 hour under a hydrogen atmosphere. The catalyst was removed by filtration and washed with methanol, the filtrate and washings were concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform/methanol/triethylamine) to yield 328 mg (54%) of the title compound in the form of a colorless solid.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol
  3. concentrationthe filtrate and washings were concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (chloroform/methanol/triethylamine)

Sources & evidence

ORD record
ord-4dc47b331b684497b3ce068c7f49a8f3
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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