1-(Hydroxymethyl)-4-propylpyrrolidin-2-one → HCID 53629122, compound

HRID 2043644Notes

Reaction equation

HRID 2043644 reaction equation
[C:1]1([C:7]2[CH:15]=[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[CH2:17][N:18]1[CH2:22][CH:21]([CH2:23][CH2:24][CH3:25])[CH2:20][C:19]1=[O:26]>FC(F)(F)C(O)=O>[C:1]1([C:7]2[C:15]([CH2:17][N:18]3[CH2:22][CH:21]([CH2:23][CH2:24][CH3:25])[CH2:20][C:19]3=[O:26])=[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 113326021-(Hydroxymethyl)-4-propylpyrrolidin-2-oneHCID 12718652HCID 12718652, compound

Product 1

HCID 53629122HCID 53629122, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2-phenylpyrazolo[1,5-a]pyrimidine x124 (25.6 mmol, 1 eq, 5 g) in trifluoroacetic acid (150 ml) is added 1-(hydroxymethyl)-4-propylpyrrolidin-2-one x2 (38.4 mmol, 1.5 eq, 6 g). The resulting solution is stirred at room temperature for three days. The solvent is removed under reduce pressure, ice is added and the mixture is alkalinized by solid NaHCO3. The mixture is extracted by AcOEt, the organic layers are washed with brine and dried over Na2SO4. The solvent is removed under reduce pressure and the crude reaction mixture purified by chromatography on silicagel (AcOEt/hexane 40/60). After crystallisation in AcOEt/hexane, to afford 2.06 g of 1-[(2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]-4-propylpyrrolidin-2-one 191 are obtained.

Workup

  1. customThe solvent is removed
  2. additionis added
  3. extractionThe mixture is extracted by AcOEt
  4. washthe organic layers are washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent is removed
  7. customthe crude reaction mixture
  8. custompurified by chromatography on silicagel (AcOEt/hexane 40/60)
  9. customAfter crystallisation in AcOEt/hexane

Sources & evidence

ORD record
ord-bbf9de6386a44f0fb2b18aba067e4784
Source dataset
uspto-grants-2013_11
Patent number
US08586623B2

Reaction notes

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