Sodium borohydride → 2-Chloro-4-{[(3S)-1-(2-hydroxyethyl)-5-oxo-3-pyrrolidinyl][(2-methylphenyl)methyl]amino}benzonitrile

HRID 1160419Notes

Reaction equation

HRID 1160419 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([N:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[C@H:11]2[CH2:15][C:14](=[O:16])[N:13]([CH2:17][CH:18]=[O:19])[CH2:12]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:9]=[C:8]([N:10]([C@H:11]2[CH2:15][C:14](=[O:16])[N:13]([CH2:17][CH2:18][OH:19])[CH2:12]2)[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 595161812-Chloro-4-{[(2-methylphenyl)methyl][(3S)-5-oxo-1-(2-oxoethyl)-3-pyrrolidinyl]amino}benzonitrile

Product 1

HCID 595162362-Chloro-4-{[(3S)-1-(2-hydroxyethyl)-5-oxo-3-pyrrolidinyl][(2-methylphenyl)methyl]amino}benzonitrileYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-4-{[(2-methylphenyl)methyl][(3S)-5-oxo-1-(2-oxoethyl)-3-pyrrolidinyl]amino}benzonitrile from the previous step was dissolved in THF, and NaBH4 (1.2 eq) was added. After stirring at room temperature for 2 h, the reaction mixture was quenched with H2O and extracted three times with ethyl acetate (5 mL). The organics were dried over anhydrous MgSO4 and concentrated to give the titled compound as white solid (3.5 g, 33% for two steps). LC-MS (ES) m/e 384.6 (M+H)+.

Workup

  1. customthe reaction mixture was quenched with H2O
  2. extractionextracted three times with ethyl acetate (5 mL)
  3. dry with materialThe organics were dried over anhydrous MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-32e162ce334c4c4eac29ccd63f70fe87
Source dataset
uspto-grants-2010_10
Patent number
US07816395B2

Reaction notes

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