N-Methylundec-10-ynamide was prepared following GP1 from undec-10-ynoic acid (2000 mg, 10.97 mmol) and methylamine (2 M in THF), the solvent was removed in vacuo, residue partitioned between DCM (20 mL) and 10% citric acid (10 mL), the organic phase extracted with 1 M sodium hydroxide (10 mL), dried with sodium sulphate, and the solvent was removed in vacuo. The crude amide was dissolved in anhydrous THF (10 mL), lithium aluminum hydride solution (9.1 mL, 2.0 eq., 2.4 M in THF) was added slowly with stirring under Ar. The reaction mixture was stirred at 50 °C for 12 h and then while being cooled on an icebath, cautiously quenched with brine. The resulting grey solids were suspended in Et 2 O (50 mL), sonicated in an ultrasonic cleaning bath for 5 minutes, filtered, and washed with Et 2 (2 × 20 mL). The ethereal extracts were dried over sodium sulphate, filtered, and volatile components evaporated in vacuo to afford N-methylundec-10-yn-1-amine .