Water → HCID 23122083, compound

HRID 1713538Notes

Reaction equation

HRID 1713538 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([NH:13][CH:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15](OC)=[O:16])=[O:12])[CH2:10][CH:5]2[C:4]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:3]1.[BH4-].[Li+].O>O1CCCC1>[OH:16][CH2:15][CH:14]([NH:13][C:11]([N:9]1[CH2:8][CH2:7][N:6]2[C:2](=[O:1])[O:3][C:4]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:5]2[CH2:10]1)=[O:12])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 23121977HCID 23121977, compound

Product 1

HCID 23122083HCID 23122083, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl α-[[(tetrahydro-3-oxo-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-7(1H)-yl)carbonyl]amino]benzeneacetate (0.15 g, 0.31 mmol) was dissolved in tetrahydrofuran (2 mL). Lithium borohydride (14 mg, 0.64 mmol) was added thereto, and the mixture was stirred at room temperature for 2 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 residue was purified with silica gel column chromatography (ethyl acetate) and powder was formed from hexane to obtain the title compound (0.13 g, yield 90%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (ethyl acetate)
  5. custompowder was formed from hexane

Sources & evidence

ORD record
ord-c5009f13f8b346489fa75d416ef667df
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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