Water → HCID 86642707, compound

Participants

Reaction Conditions

Reaction Steps

3-Azido-N-dodecyl-N,3-dimethylbutanamide (7.28 g, 22.4 mmol) was dissolved into anhydrous THF (50 mL) and added dropwise to a suspension of LAH (1.70 g, 2.0 equiv, 44.8 mmol) in anhydrous THF (100 mL) to maintain the reaction at reflux (30 min). After complete addition, the flask was fitted with a condenser and the reaction heated in a 70° C. oil bath for 8 h. The reaction mixture was cooled in an ice bath and water (1.7 mL) was added dropwise over 20 min. Then 15% NaOH solution (1.7 mL) was added dropwise over 10 min. The suspension was stirred for a further 10 min and water (1.7 mL) was added in one portion and the mixture stirred for 30 min to a give fine white suspension. The suspension was filtered through a pad of Celite® and washed with diethyl ether (2×100 mL). The combined filtrate was concentrated with a bath temperature between 10-13° C. to an orange liquid (5.61 g, 88.0%). LRMS (ESI+) for C18H40N2 (284.3); Found: 285 (MH+).

Provenance & Evidence