Cesium carbonate → racemic (2'R,3R,4'S)-1'-(aminocarbonyl-methyl)-6-bromo-4'-(3-chlorophenyl)-2'-(1-methyl cyclopropyl)-2,3-dihydro-2,6'-dioxospiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

HRID 1728212Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:28])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24]3([CH3:27])[CH2:26][CH2:25]3)[C:5]2=[CH:4][CH:3]=1.[CH3:29][O:30][CH:31]([Si:33]([CH3:36])([CH3:35])[CH3:34])[CH3:32].Br[CH2:38][C:39]([NH2:41])=[O:40].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[NH2:41][C:39]([CH2:38][N:12]1[C:13](=[O:23])[CH2:14][CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[C:10]2([C:5]3[C:6](=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)[NH:8][C:9]2=[O:28])[CH:11]1[C:24]1([CH3:27])[CH2:25][CH2:26]1)=[O:40].[CH3:29][O:30][CH:31]([Si:33]([CH3:36])([CH3:35])[CH3:34])[CH3:32]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of racemic (2′R,3R,4′S)-6-bromo-4′-(3-chlorophenyl)-2′-(1-methyl cyclopropyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (800 mg, 1.36 mmol) and 2-bromo-acetamide (938 mg, 6.8 mmol) in DMF (1 mL) was added Cs2CO3 (4.4 g, 13.4 mmol). The mixture was stirred at 50° C. for 1.5 h, then purified by column chromatography to give title compound (60 mg, 6.8%).

Workup

custompurified by column chromatography

Sources & evidence

ORD record: ord-6bc38e3f3a02476abdafb16a6e86b49a
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495007B2

Reaction notes

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