Water → HCID 23122010, compound

HRID 1713554Notes

Reaction equation

HRID 1713554 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.Br[CH2:24][CH2:25][N:26]=[C:27]=[O:28].[NH:29]1[CH2:33][CH:32]=[CH:31][CH2:30]1.O>O1CCCC1>[O:16]=[C:9]1[N:10]2[CH2:15][CH2:14][N:13]([C:27]([NH:26][CH2:25][CH2:24][N:29]3[CH:33]=[CH:32][CH:31]=[CH:30]3)=[O:28])[CH2:12][CH:11]2[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[O:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 660593-PyrrolineHCID 42559572-Bromoethyl isocyanateHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23122010HCID 23122010, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.20 g, 0.68 mmol) was dissolved in tetrahydrofuran (7 mL). 2-Bromoethyl isocyanate (0.07 mL, 0.77 mmol) was added thereto at 0° C., and the mixture was stirred for 1 hour without modification. The reaction solution was concentrated under reduced pressure and dissolved in N-methyl-2-pyrrolidinone (7 mL). 3-Pyrroline (0.21 mL, 2.7 mmol) was added thereto, and the mixture was stirred at 60° C. for 25 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. Then, the organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, water and saturated brine, and dried over magnesium sulfate. The solid was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified with amino silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate) and silica gel column chromatography (hexane:ethyl acetate=8:2 to ethyl acetate) to obtain the title compound (0.21 g, yield 72%) as amorphous.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutiondissolved in N-methyl-2-pyrrolidinone (7 mL)
  3. stirringthe mixture was stirred at 60° C. for 25 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThen, the organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe solid was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified with amino silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate) and silica gel column chromatography (hexane:ethyl acetate=8:2 to ethyl acetate)

Sources & evidence

ORD record
ord-58b43d9fd42f4a7c91aa6c4e0c2900e4
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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