Methanol → racemic (2'R,3R,4'S)-6-chloro-4'-(3-cyano-phenyl)-2'-(1-methylene-propyl) spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728075Notes

Reaction equation

HRID 1728075 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:12]/[C:13]3[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=3)[C:16]#[N:17])/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH2:21]=[C:22]([CH:25]=[N:26][C:27]([O:29][Si](C)(C)C)=[CH2:28])[CH2:23][CH3:24].CO>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[C:9]2[NH:8][C:7](=[O:11])[C:6]3([CH:12]([C:13]4[CH:20]=[CH:19][CH:18]=[C:15]([C:16]#[N:17])[CH:14]=4)[CH2:28][C:27](=[O:29])[NH:26][CH:25]3[C:22](=[CH2:21])[CH2:23][CH3:24])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 71246038Z-3-(6-Chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-benzonitrileHCID 76567901HCID 76567901, compound

Product 1

HCID 76568141racemic (2'R,3R,4'S)-6-chloro-4'-(3-cyano-phenyl)-2'-(1-methylene-propyl) spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

E/Z-3-(6-Chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-benzonitrile (280 mg, 1 mmol) prepared in example 134a was heated with 1-(1-methylene-propyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene freshly prepared in example 80a (2.06 g, 10.5 mmol) in toluene (20 mL) in a sealed tube at 135° C. for 1 h, then cooled to room temperature. Methanol (80 mL) was added, and the mixture was filtered through a short pad of celite. The filtrate was concentrated, the residue was purified by chromatography (EtOAc) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-cyano-phenyl)-2′-(1-methylene-propyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a solid (180 mg, 35%).

Workup

  1. filtrationthe mixture was filtered through a short pad of celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by chromatography (EtOAc)

Sources & evidence

ORD record
ord-f049f4287c504eaea07895a0cc08bc02
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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