1-(4-Aminophenyl)-1-propanol → (2e,4e,6e,8e)-3,7-Dimethyl-n-(pyridin-4-yl)-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenamide

Participants

Reaction Steps

Coupling of (4-amino)phenylpropanol (453 mg; 3 mmol) and retinoic acid (600 mg, 2 mmol) in anhydrous DMF (4 mL) using standard EDC/HOBt coupling condtions yielded the desired amide as a pale, yellow solid (600 mg, 69%). EIMS m/z: 434 ([M+1]+). The amide (510 mg, 1.2 mmol) was dissolved in CH2Cl2 (4 mL) and added with triethylamine (276 □L, 2 mmol) and DMAP (10 mg). The reaction mixture was then treated with p-toluenesulfonyl chloride (324 mg, 1.7 mmol) and stirred at room temperature overnight. The reaction mixture was then diluted with CH2Cl2 (10 mL) and washed with water (2×10 mL) and brine (10 mL). The organic layer was dried over Na2SO4. The solvent was removed in vacuo to afford tosylate which was used without further purification.

Provenance & Evidence