Ammonia → 101901-50-2

Participants

Reaction Steps

A solution of 3,5-dimethyl-1-adamantanecarboxylic acid (2.51 g, 12.1 mmol) in dry pyridine (40 mL) at 0° C. was treated dropwise with methanesulphonyl chloride (1.4 g, 12.2 nmmol), stirred for 2 h, saturated with ammonia gas, stirred for 5 min and the excess ammonia removed in vacuo. The resulting suspension at 0° C. was treated with methanesulphonyl chloride (11.8 g, 102 mmol), stirred overnight at room temperature, poured into cold 1-M HCl (200 mL) and extracted with EtOAc (3×40 mL). The organic phase was washed with dilute HCl (50 mL), water (50 mL), dried (MgSO4), concentrated in vacuo and the residue purified by chromatography [SiO2; CH2Cl2] to give the product (1.97 g, 86%) as a pale brown oil: IR νmax (liquid film)/cm−1 2922, 2849, 2235, 1455, 1359 and 1098; NMR δH (400 MHz, CDCl3) 0.87 (6H, s), 1.19 (2H, s), 1.3-1.45 (4H, m), 1.55-1.75 (4H, m), 1.8-1.9 (2H, m) and 2.1-2.15 (1H, m).

Provenance & Evidence