4-Toluenesulfonyl chloride → HCID 53829184, compound

HRID 1614830Notes

Reaction equation

HRID 1614830 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:9][CH2:10][O:11][CH2:12][CH2:13]O)=[CH:4][CH:3]=1.C([Li])CCC.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[NH:38]1[CH2:43][CH2:42][CH2:41][C@@H:40]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:39]1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH2:47]([O:46][C:44]([C@@H:40]1[CH2:41][CH2:42][CH2:43][N:38]([CH2:13][CH2:12][O:11][CH2:10][CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:39]1)=[O:45])[CH3:48]

Participants

7

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 185582ethyl (3R)-piperidine-3-carboxylateHCID 10782137HCID 10782137, compoundHCID 178418339Butyllithium

Product 1

HCID 53829184HCID 53829184, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

A solution of 2-(3,3-bis(4-chlorophenyl)-2-propen-1-yloxy)ethanol (4.0 g, 12.4 mmol) in dry THF (25 ml) kept under a nitrogen atmosphere was cooled to 10° C. and a solution of n-butyllithium in hexanes (5.4 ml, 2.5 M) was added dropwise. The reaction mixture was stirred for 15 minutes at room temperature and p-toluenesulphonyl chloride (2.6 g, 13.8 mmol) was added. The mixture was stirred at room temperature for 1 h. Ethyl (R)-3-piperidinecarboxylate (1.9 g, 12.1 mmol) and potassium carbonate (3.4 g, 24.6 mmol) were added and the mixture was heated at reflux temperature for 18 h. To the cooled reaction mixture THF (50 ml) was added. The mixture was filtered and the solvent evaporated in vacuo. Flash chromatography of the residue on silica gel (100 g) using a mixture of n-heptane and ethyl acetate (3:2) as eluent provided 0.6 g (11%) of the title compound as an oil. 1H NMR (CDCl3)δ 4.02 (d, 2H); 6.20 (t, 1H).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. temperaturethe mixture was heated
  3. temperatureat reflux temperature for 18 h
  4. additionwas added
  5. filtrationThe mixture was filtered
  6. customthe solvent evaporated in vacuo
  7. additiona mixture of n-heptane and ethyl acetate (3:2) as eluent

Sources & evidence

ORD record
ord-02132bbff3c0497e9facb28604c78b0e
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

Loading…