Methanol → racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-2'-(1-methylene-propyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

HRID 1728094Notes

Reaction equation

[CH2:1]=[C:2]([CH:5]=[N:6][C:7]([O:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=[CH2:8])[CH2:3][CH3:4].[Br:14][C:15]1[CH:23]=[C:22]2[C:18](/[C:19](=[CH:33]/[C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=3)/[C:20](=[O:32])[N:21]2[CH2:24][O:25][CH2:26][CH2:27][Si](C)(C)C)=[CH:17][CH:16]=1.CO>C1(C)C=CC=CC=1>[Br:14][C:15]1[CH:23]=[C:22]2[NH:21][C:20](=[O:32])[C:19]3([CH:33]([C:34]4[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=4)[CH2:8][C:7](=[O:9])[NH:6][CH:5]3[C:2](=[CH2:1])[CH2:3][CH3:4])[C:18]2=[CH:17][CH:16]=1.[CH3:24][O:25][CH:26]([Si:10]([CH3:11])([CH3:12])[CH3:13])[CH3:27]

Participants

Conditions

Temperature: 135 °C

Procedure

To a solution of 1-(1-ethyl-ethenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (42 mmol) prepared in example 80a in toluene (50 mL) was added E/Z-6-Bromo-3-(3-chloro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indole-2-one (2 g, 4.3 mmol) prepared in example 161a. The reaction mixture was stirred under nitrogen in a sealed tube at 135° C. for 1 h. After cooling to room temperature, methanol (100 mL) was added, and then the mixture was concentrated. The residue was purified by chromatography (EtOAc:Hexane=2:1) gave racemic (2′R,3R,4′S)-6-bromo-4′-(3-chlorophenyl)-2′-(1-methylene-propyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane as a solid (Yield 350 mg).

Workup

temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated
customThe residue was purified by chromatography (EtOAc:Hexane=2:1)

Sources & evidence

ORD record: ord-63a309682a104421ac0aeb08f82f069c
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495007B2

Reaction notes

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