Water → HCID 86674634, compound

HRID 245666Notes

Reaction equation

HRID 245666 reaction equation
[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([C@@H:12]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13]2)=O)=[N:4][CH:5]=[CH:6][N:7]=1.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+].O>C(OCC)(=O)C.CN(C)C=O>[Cl:1][C:2]1[C:3]2[N:4]([C:10]([C@@H:12]3[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:18])[CH2:13]3)=[N:9][CH:8]=2)[CH:5]=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 86674635HCID 86674635, compound

Product 1

HCID 86674634HCID 86674634, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(R)-Benzyl 3-((3-chloropyrazin-2-yl)methylcarbamoyl)pyrrolidine-1-carboxylate (5.90 mmol, 2.21 g) was dissolved in ethyl acetate (20 ml) and N,N-dimethylformamide (1.538 ml). The stirred reaction mixture was cooled to 0° C. and phosphorous oxychloride (23.58 mmol, 2.198 mL) was added. After stirring at room temperature for 3 hours the reaction mixture was cooled to 0° C. and an excess of solid sodium hydrogencarbonate was added. The suspension was stirred at 0° C. for 10 minutes and 20 minutes at room temperature. Then it was cooled to 0° C. and water was added. The organic layer was separated and the aqueous layer extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (sodium sulfate) and concentrated in vacuo to yield (R)-benzyl 3-(8-chloroimidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate (2.11 g).

Workup

  1. customThe stirred reaction mixture
  2. temperaturewas cooled to 0° C.
  3. stirringThe suspension was stirred at 0° C. for 10 minutes and 20 minutes at room temperature
  4. temperatureThen it was cooled to 0° C.
  5. customThe organic layer was separated
  6. extractionthe aqueous layer extracted three times with ethyl acetate
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43dbebe5ca784ec4aeaf2da84bffaf38
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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