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
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]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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.