Iodoethane → racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-1'-ethyl-2,3-dihydro-2'-(2-methylphenyl)-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid tert-butyl ester

HRID 1727987Notes

Reaction equation

HRID 1727987 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([Cl:37])[CH:35]=2)[C:10]2([CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[CH2:14][C:13](=[O:23])[NH:12][CH:11]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[C:9]1=[O:38])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Li+].I[CH2:42][CH3:43]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([Cl:37])[CH:35]=2)[C:10]2([CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[CH2:14][C:13](=[O:23])[N:12]([CH2:42][CH3:43])[CH:11]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[C:9]1=[O:38])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 62714Lithium hydrideHCID 90866629racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-2,3-dihydro-2'-(2-methylphenyl)-2,6'-dioxospiro[indole-3,3'-piperidine]-1-carboxylic acid tert-butyl ester

Product 1

HCID 90883474racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-1'-ethyl-2,3-dihydro-2'-(2-methylphenyl)-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid tert-butyl esterYield 63.9%

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-chlorophenyl)-2,3-dihydro-2′-(2-methylphenyl-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid tert-butyl ester (0.3 g, 0.54 mmol) prepared in example 24b was reacted with LiH (86 mg, 10.9 mmol) (Aldrich) and iodoethane (2 mL, 25 mmol) in N,N-dimethyl-formamide to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-1′-ethyl-2,3-dihydro-2′-(2-methylphenyl)-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid tert-butyl ester as a white foam (Yield: 0.2 g, 63%).

Sources & evidence

ORD record
ord-b4fce9b113da4f43b57ae679d2acc132
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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