Benzyl Alcohol → (R)-N-Cbz-2,6-dimethyl-5-hepten-1-amine

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Diphenylphosphoryl azide (14 mL, 65 mmol) was added dropwise to a solution of (R)-citronellic acid (10 g, 59 mmol) and triethylamine (9.1 mL, 65mmol) in 60 mL of toluene. The mixture was heated for 1 hr at 80° C. 12 mL (120 mmol) of benzyl alcohol was added and the mixture was heated to reflux for 4 hrs. The reaction mixture was cooled, diluted with ethyl acetate and washed with water, saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was removed in vacuo to give a crude product which was purified on silica gel using 5% ethyl acetate in hexane as solvent to afford 9.8 g of the desired carbamate as a thick oil.

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