1-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → racemic (2'R,3R,4'S)-6-chloro-4'-(2,2-dimethylpropyl)-2'-(5-fluoro-2-methyl phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728088Notes

Reaction equation

HRID 1728088 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:12]/[CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[F:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:34])=[C:23]([CH:25]=[N:26][C:27]([O:29][Si](C)(C)C)=[CH2:28])[CH:24]=1>>[Cl:1][C:2]1[CH:10]=[C:9]2[NH:8][C:7](=[O:11])[C:6]3([CH:12]([CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:28][C:27](=[O:29])[NH:26][CH:25]3[C:23]3[CH:24]=[C:19]([F:18])[CH:20]=[CH:21][C:22]=3[CH3:34])[C:5]2=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 701785041-(5-Fluoro-2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86615083Z-6-chloro-3-(3,3-dimethyl-butylidene)-1,3-dihydro-indol-2-one

Product 1

HCID 76568127racemic (2'R,3R,4'S)-6-chloro-4'-(2,2-dimethylpropyl)-2'-(5-fluoro-2-methyl phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Procedure

In a manner similar to the method described in example 1c, E/Z-6-Chloro-3-(3,3-dimethyl-butylidene)-1,3-dihydro-indol-2-one (0.2 g, 0.80 mmol) prepared in example 1a was reacted with 1-(5-fluoro-2-methyl-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene prepared in example 36a to give racemic (2′R,3R,4′S)-6-chloro-4′-(2,2-dimethylpropyl)-2′-(5-fluoro-2-methyl phenyl)-spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as an white solid (7 mg).

Sources & evidence

ORD record
ord-3fcf788d09a14b98baf842115c889ff8
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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