Pyridine → Hexahydro-1,1-diphenyl-7-(phenylsulfonyl)-3H-oxazolo[3,4-a]pyrazin-3-one

HRID 1713528Notes

Reaction equation

HRID 1713528 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:29]1([S:35](Cl)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)(Cl)Cl>[C:17]1([C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:11]3[CH2:12][N:13]([S:35]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)(=[O:37])=[O:36])[CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23122059Hexahydro-1,1-diphenyl-7-(phenylsulfonyl)-3H-oxazolo[3,4-a]pyrazin-3-oneYield 37%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (50 mg, 0.17 mmol) in chloroform (2 mL) were sequentially added pyridine (0.5 mL) and benzenesulfonyl chloride (43 mg, 0.24 mmol), and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1) and crystallized from diisopropyl ether to obtain the title compound (27 mg, yield 37%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1)
  3. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-5e67749ca9454e8081e3cc38d763fb1e
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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