Methanol → HCID 71251997, compound

HRID 2411708Notes

Reaction equation

HRID 2411708 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=4[CH3:32])[CH2:21][CH2:20]3)=[O:18])=[CH:13][CH:12]=2)[CH2:6]1)=O.O1CCCC1.[BH4-].[Na+].CO>O>[CH3:32][C:26]1[CH:27]=[C:28]([CH3:31])[CH:29]=[CH:30][C:25]=1[N:22]1[CH2:23][CH2:24][N:19]([C:17]([C:14]2[CH:15]=[CH:16][C:11]([N:7]3[CH2:6][CH:5]([CH2:3][OH:2])[CH2:9][C:8]3=[O:10])=[CH:12][CH:13]=2)=[O:18])[CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 71252715HCID 71252715, compound

Product 1

HCID 71251997HCID 71251997, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1-{4-[4-(2,4-dimethylphenyl)piperazine-carbonyl]phenyl}-5-oxopyrrolidine-3-carboxylic acid methyl ester (1.3 g) described in Example 337 were added tetrahydrofuran (5 mL) and sodium borohydride (124 mg), methanol (0.9 mL) was added with heating under reflux, and the mixture was stirred for 1 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give the title compound (1.06 g).

Workup

  1. additionwas added
  2. temperaturewith heating
  3. temperatureunder reflux
  4. temperatureThe reaction mixture was cooled
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. customthe solvent was evaporated
  8. customThe obtained residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-ab132dae8d374782b4b96640b4c363d1
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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