Water → HCID 23122033, compound

HRID 1713512Notes

Reaction equation

HRID 1713512 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.C(N(C(C)C)CC)(C)C.[CH2:32](Br)[C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34].O>O1CCCC1>[O:34]=[C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:32][N:13]1[CH2:14][CH2:15][N:10]2[C:9](=[O:16])[O:8][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:11]2[CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 81531DiisopropylethylamineHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23122033HCID 23122033, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.10 g, 0.34 mmol) in tetrahydrofuran (2 mL) were sequentially added diisopropylethylamine (0.6 mL) and phenacyl bromide (0.10 g, 0.51 mmol), and the mixture was stirred at room temperature for 17 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1), hexane was added thereto, and powder was formed to obtain the title compound (92 mg, yield 66%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1), hexane
  5. additionwas added
  6. custompowder was formed

Sources & evidence

ORD record
ord-d19f5c8966134092a4c4d39813aa2339
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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