rel-(3R,5S)-3,5-Dimethylpiperidine → 8-s-Butyl-2-(3,5-dimethylpiperidin-1-ylmethyl)-1,4-dioxaspiro[4,5] decane

HRID 1085509Notes

Reaction equation

HRID 1085509 reaction equation
[CH:1]([CH:5]1[CH2:16][CH2:15][C:8]2([O:12][CH:11]([CH2:13]Cl)[CH2:10][O:9]2)[CH2:7][CH2:6]1)([CH2:3][CH3:4])[CH3:2].[CH3:17][C@H:18]1[CH2:23][C@@H:22]([CH3:24])[CH2:21][NH:20][CH2:19]1>C(OCC)(=O)C>[CH:1]([CH:5]1[CH2:16][CH2:15][C:8]2([O:12][CH:11]([CH2:13][N:20]3[CH2:21][CH:22]([CH3:24])[CH2:23][CH:18]([CH3:17])[CH2:19]3)[CH2:10][O:9]2)[CH2:7][CH2:6]1)([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 641101rel-(3R,5S)-3,5-DimethylpiperidineHCID 146753578-s-Butyl-2-chloromethyl-1,4dioxaspiro [4,5] decane

Product 1

HCID 146753758-s-Butyl-2-(3,5-dimethylpiperidin-1-ylmethyl)-1,4-dioxaspiro[4,5] decaneYield 75.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

24.7 g (0.1 mol) of 8-s-butyl-2-chloromethyl-1,4dioxaspiro [4,5] decane and 45.2 g (0.4 mol) of cis-3,5-dimethylpiperidine are stirred at 140° C. for 16 hours and cooled, 200 ml of ethyl acetate are added, the mixture is washed three times with 200 ml of water each time, dried over sodium sulphate and concentrated in vacuo and the residue is purified by chromatography (silica gel; mobile phase: ethyl acetate). 24.3 g (75% of theory) of 8-s-butyl-2-(3,5-dimethylpiperidin-1-ylmethyl) -1,4-dioxaspiro[4,5] decane are obtained as an oil of refractive index nd20 1.4762.

Workup

  1. temperaturecooled
  2. washthe mixture is washed three times with 200 ml of water each time
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customthe residue is purified by chromatography (silica gel; mobile phase: ethyl acetate)

Sources & evidence

ORD record
ord-7e3144fcf3b446e3a1e72215ac73bf4d
Source dataset
uspto-grants-1991_04
Patent number
US05010101

Reaction notes

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