2-chloro-4-[(2S,3S,4S)-3-hydroxy-2-methyl-4-(2-methylprop-2-en-1-yl)-5-oxopyrrolidin-1-yl]benzonitrile → 2-chloro-4-[(2S,3S,4S)-3-hydroxy-4-isobutyl-2-methyl-5-oxopyrrolidin-1-yl]benzonitrile

HRID 1967364Notes

Reaction equation

HRID 1967364 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[C:14](=[O:15])[C@@H:13]([CH2:16][C:17]([CH3:19])=[CH2:18])[C@H:12]([OH:20])[C@@H:11]2[CH3:21])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]>CO.[Pd]>[Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[C:14](=[O:15])[C@@H:13]([CH2:16][CH:17]([CH3:18])[CH3:19])[C@H:12]([OH:20])[C@@H:11]2[CH3:21])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 1

HCID 595568992-chloro-4-[(2S,3S,4S)-3-hydroxy-2-methyl-4-(2-methylprop-2-en-1-yl)-5-oxopyrrolidin-1-yl]benzonitrile

Product 1

HCID 595568962-chloro-4-[(2S,3S,4S)-3-hydroxy-4-isobutyl-2-methyl-5-oxopyrrolidin-1-yl]benzonitrileYield 19.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-chloro-4-[(2S,3S,4S)-3-hydroxy-2-methyl-4-(2-methylprop-2-en-1-yl)-5-oxopyrrolidin-1-yl]benzonitrile (22.3 mg) in methanol (3.0 mL) was added palladium/fibroin (12.0 mg), and the mixture was stirred for 48 hr under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/1) to give the title compound as a pale-yellow oil (yield: 4.3 mg, 19.1%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/1)

Sources & evidence

ORD record
ord-efc244c939af4582a8c9af98613fb9b3
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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