Potassium Iodide → HCID 54307972, compound

HRID 1614825Notes

Reaction equation

HRID 1614825 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22])=[CH:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14]O.C([Li])CCC.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[NH:39]1[CH2:44][CH2:43][CH2:42][C@@H:41]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:40]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C1(C)C=CC=CC=1.CC(C)=O>[CH2:48]([O:47][C:45]([C@@H:41]1[CH2:42][CH2:43][CH2:44][N:39]([CH2:14][CH2:13][CH2:12][O:11][CH2:10][CH:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[CH2:40]1)=[O:46])[CH3:49]

Participants

9

Reactant 6

HCID 4875Potassium IodideHCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 185582ethyl (3R)-piperidine-3-carboxylateHCID 107563633-(3,3-Bis(2-methylphenyl)-2-propen-1-yloxy)-1-propanolHCID 178418339Butyllithium

Product 1

HCID 54307972HCID 54307972, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 1140TolueneSolvent

Procedure

A solution of 3-(3,3-bis(2-methylphenyl)-2-propen-1-yloxy)-1-propanol (3.45 g, 11.6 mmol) in dry toluene (150 ml) was cooled in an ice-bath and a solution of n-butyllithium in hexanes (5.1 ml, 2.5 M) was added dropwise. The reaction mixture was stirred for 15 minutes at room temperature and p-toluenesulphonyl chloride (2.44 g, 12.8 mmol) was added. The mixture was stirred at room temperature for 3 h. Ethyl (R)-3-piperidinecarboxylate (4.5 g, 23.3 mmol) and potassium carbonate (3.2 g, 23.3 mmol) were added and the mixture was stirred at room temperature for 0.5 h and then at 75° C. for 12 h. Potassium iodide (1.0 g) and acetone (40 ml) were added and the mixture was heated at reflux temperature for 15 h. Acetone (50 ml) was added and the cooled reaction mixture was filtered and the solvent evaporated in vacuo. Flash chromatography of the residue on silica gel (280 g) using a gradient of n-heptane in ethyl acetate as eluent afforded 2.6 g (52%) of (R)-N-(3-(3,3-bis(2-methylphenyl)-2-propen-1-yloxy)-1-propyl)3-piperidinecarboxylic acid ethyl ester as an oil. TLC: rf=0.52 (SiO2 ; methanol/ethyl acetate=1:9).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 h
  2. stirringthe mixture was stirred at room temperature for 0.5 h
  3. waitat 75° C. for 12 h
  4. temperaturethe mixture was heated
  5. temperatureat reflux temperature for 15 h
  6. customthe cooled reaction mixture
  7. filtrationwas filtered
  8. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-4fb749d5b3e04d97a64e4845b1a63146
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

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