Pyridine → JK928A7Qyr

Reaction equation

[N:1]1C=CC=C[CH:2]=1.[O:7]([CH2:14][CH2:15]N)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:17]1([CH3:29])[CH2:22][CH2:21][CH:20]([CH:23]([CH3:25])[CH3:24])[CH:19]([C:26](Cl)=[O:27])[CH2:18]1.O1CCC[CH2:31]1>>[CH:23]([C@@H:20]1[CH2:21][CH2:22][C@@H:17]([CH3:29])[CH2:18][C@H:19]1[C:26]([NH:1][CH2:2][CH2:15][CH2:14][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=1[CH3:31])=[O:27])([CH3:25])[CH3:24]

Participants

Reactant 4

HCID 1049Pyridine

HCID 8028Tetrahydrofuran

HCID 156512-Phenoxyethanamine

HCID 13734319Cyclohexanecarbonyl chloride, 5-methyl-2-(1-methylethyl)-

Product 1

HCID 67299849JK928A7Qyr

Procedure

In a 25 mL round bottom flask, fitted with magnetic stirrer, 10 mL of tetrahydrofurane, 6.0 mmol (1.5 eq.) of pyridine and 3.33 mmol of 2-phenoxyethanamine were added. p-Menthane carboxylic acid chloride (4.0 mmol) were added and the mixture was stirred at room temperature for 16 hours, over night. The reaction mixture was extracted with MTBE and HCl (1N in water). The organic layer was washed with NaOH (1N in water), dried over MgSO4 and concentrated. The crude product was purified by column chromatography or crystallized from MtBE and Hexane under dry ice cooling.