Lithium hydride → 6-Chloro-4'-(3-chloro-phenyl)-1'-(3-chloro-propyl)-2'-(1-ethyl-propenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

HRID 1728030Notes

Reaction equation

HRID 1728030 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:29])[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]([CH2:27][CH3:28])=[CH:25][CH3:26])[C:5]2=[CH:4][CH:3]=1.[CH3:30][O:31][CH:32]([Si:34]([CH3:37])([CH3:36])[CH3:35])[CH3:33].[H-].[Li+].[Cl:40][CH2:41][CH2:42][CH2:43]I>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:29])[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])[N:12]([CH2:43][CH2:42][CH2:41][Cl:40])[CH:11]3[C:24]([CH2:27][CH3:28])=[CH:25][CH3:26])[C:5]2=[CH:4][CH:3]=1.[CH3:30][O:31][CH:32]([Si:34]([CH3:37])([CH3:36])[CH3:35])[CH3:33]

Participants

5

Reactant 3

HCID 62714Lithium hydrideHCID 813631-Chloro-3-iodopropaneHCID 775800716-Chloro-4'-(3-chloro-phenyl)-2'-(1-ethyl-propenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

Product 1

HCID 775800946-Chloro-4'-(3-chloro-phenyl)-1'-(3-chloro-propyl)-2'-(1-ethyl-propenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to the method described in example 24c, racemic (2′R,3R,4′S)-6-chloro-4′-(3-chloro-phenyl)-2′-(1-ethyl-propenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (2.4 g, 4.3 mmol) prepared in example 81a was reacted with LiH (1 g, 125 mmol) and 1-chloro-3-iodo-propane (8 g, 39 mmol) in N,N-dimethyl-formamide (40 mL) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chloro-phenyl)-1′-(3-chloro-propyl)-2′-(1-ethyl-propenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane as a white form (Yield: 0.61 g, 22%).

Sources & evidence

ORD record
ord-c7bc0ade370141358afafae1e86b2f72
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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