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Chloroform → (1-Methyl-7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydroquinol-4-yl-methane-sulfonyl)-piperidine-4-carboxylic acid methyl ester

HRID 84146
Notes
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Reaction equation

HRID 84146 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([S:11]([CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25]C)[C:17]([CH3:28])([CH3:27])[CH:16]=2)(=[O:13])=[O:12])[CH2:7][CH2:6]1)=[O:4].CN1C2C(=CC=[C:37]([O:40]C)C=2)C(CS(Cl)(=O)=O)CC1(C)C.COC(C1CCNCC1)=O.C(Cl)(Cl)Cl>C(#N)C.C(O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([S:11]([CH2:14][CH:15]2[C:24]3[C:19](=[CH:20][C:21]([O:40][CH3:37])=[CH:22][CH:23]=3)[N:18]([CH3:25])[C:17]([CH3:27])([CH3:28])[CH2:16]2)(=[O:12])=[O:13])[CH2:7][CH2:6]1)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6212ChloroformHCID 424914Methyl isonipecotateHCID 12138183(1-Ethyl-2,2-dimethyl-1,2-dihydroquinol-4-yl-methanesulfonyl)-piperidine-4-carboxylic acid methyl esterHCID 12138193(1-Methyl-7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydroquinol-4-yl)-methane-sulfonic acid chloride

Product 1

HCID 12138194
(1-Methyl-7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydroquinol-4-yl-methane-sulfonyl)-piperidine-4-carboxylic acid methyl ester
Yield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

(1-Methyl-7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydroquinol-4-yl-methane-sulfonyl)-piperidine-4-carboxylic acid methyl ester (20) is prepared similarly to compound (10) from compound (19) and 4-piperidinecarboxylic acid methyl ester in dry acetonitrile. It is isolated by column chromatography on silica gel using a gradient running from chloroform to ethanol.

Workup

  1. customIt is isolated by column chromatography on silica gel using a gradient

Sources & evidence

ORD record
ord-63e10f8f54a940598f5f9681467ddd15
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846924B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes