HCID 76567901, compound → HCID 77580212, compound

HRID 1728038Notes

Reaction equation

HRID 1728038 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:20]/[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)/[C:7](=[O:19])[N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si](C)(C)C)=[CH:4][CH:3]=1.[CH2:28]=[C:29]([CH:32]=[N:33][C:34]([O:36][Si:37]([CH3:40])([CH3:39])[CH3:38])=[CH2:35])[CH2:30][CH3:31]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[C:9]2[NH:8][C:7](=[O:19])[C:6]3([CH:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=4)[CH2:35][C:34](=[O:36])[NH:33][CH:32]3[C:29](=[CH2:28])[CH2:30][CH3:31])[C:5]2=[CH:4][CH:3]=1.[CH3:11][O:12][CH:13]([Si:37]([CH3:38])([CH3:39])[CH3:40])[CH3:14]

Participants

4

Reactant 2

HCID 76567901HCID 76567901, compoundHCID 86615089Z-6-chloro-3-(3-chloro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indole-2-one

Product 1

HCID 77580212HCID 77580212, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in example 55b, E/Z-6-chloro-3-(3-chloro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indole-2-one (3 g, 7.1 mmol) prepared in example 55a was reacted with 1-(1-methylene-propyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (19 g, 96 mmol) prepared in example 80a in toluene (200 mL) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chloro-phenyl)-2′-(1-methylene-propyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane as a white foam (Yield 3.5 g, 90%).

Sources & evidence

ORD record
ord-d80ae9dfabf949dcb778346acbf69d5f
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

Loading…