Water → HCID 23121861, compound

HRID 1713539Notes

Reaction equation

HRID 1713539 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([NH:13][CH2:14][NH:15][C:16]([N:18]=[N+]=[N-])=[O:17])=[O:12])[CH2:10][CH:5]2[C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:3]1.[BH4-].[Na+].O>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:18][C:16]([NH:15][CH2:14][NH:13][C:11]([N:9]1[CH2:8][CH2:7][N:6]2[C:2](=[O:1])[O:3][C:4]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:5]2[CH2:10]1)=[O:12])=[O:17]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86611651HCID 86611651, compound

Product 1

HCID 23121861HCID 23121861, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

[[[(Tetrahydro-3-oxo-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-7(1H)-yl)carbonyl]amino]methyl]carbamic azide (68 mg, 0.16 mmol) was dissolved in methanol (3 mL). Nickel (II) chloride hexahydrate (77 mg, 0.32 mmol) and sodium borohydride (12 mg, 0.32 mmol) were added thereto, and the mixture was stirred at room temperature for 4 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then concentrated under reduced pressure. The precipitated powder was washed with diisopropyl ether and dried to obtain the title compound (52 mg, yield 81%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. concentrationconcentrated under reduced pressure
  4. washThe precipitated powder was washed with diisopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-18948810d72c4aa58dc06d40f453f8a8
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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