(R)-2-Methylpiperidine → 2-phenyl-3-methyl-8-(1-(R)-[2-(R)-methylpiperidino]-2-[tert-butyldimethylsilyloxy]ethyl)quinoline

HRID 1167183Notes

Reaction equation

HRID 1167183 reaction equation
[C:1]1([C:7]2[C:16]([CH3:17])=[CH:15][C:14]3[C:9](=[C:10]([C@H:18](OS(C)(=O)=O)[CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:33][C@@H:34]1[CH2:39][CH2:38][CH2:37][CH2:36][NH:35]1>C(Cl)(Cl)Cl>[C:1]1([C:7]2[C:16]([CH3:17])=[CH:15][C:14]3[C:9](=[C:10]([C@@H:18]([N:35]4[CH2:36][CH2:37][CH2:38][CH2:39][C@H:34]4[CH3:33])[CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:25])[CH3:26])([CH3:23])[CH3:22])[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 637525(R)-2-MethylpiperidineHCID 213565452-phenyl-3-methyl-8-(1-(S)-methanesulfonyloxy-2-[tert-butyldimethylsilyloxy]ethyl)quinoline

Product 1

HCID 155214772-phenyl-3-methyl-8-(1-(R)-[2-(R)-methylpiperidino]-2-[tert-butyldimethylsilyloxy]ethyl)quinolineYield 45%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 7 g (17.8 mmol) of 2-phenyl-3-methyl-8-(1-(S)-methanesulfonyloxy-2-[tert-butyldimethylsilyloxy]ethyl)quinoline 8.8 g (88 mmol) of 2-(R)-methylpiperidine in 50 ml of anhydrous chloroform is brought to 60° C. for 6 hours. The reaction mixture is concentrated under vacuum and the residue obtained is purified by silica gel chromatography (eluent: dichloromethane/methanol 9/1) to provide 3.8 g of 2-phenyl-3-methyl-8-(1-(R)-[2-(R)-methylpiperidino]-2-[tert-butyldimethylsilyloxy]ethyl)quinoline in the form of a colorless oil. (Yield: 45%)

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. customthe residue obtained
  3. customis purified by silica gel chromatography (eluent: dichloromethane/methanol 9/1)

Sources & evidence

ORD record
ord-5fe72ba77e914226b67387de1f4f95f8
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

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