Tricyclo[3.3.1.13,7]decan-1-amine hydrochloride
A solution of acetamide (0.97 g, 5.0 mmol) in dry THF (15 mL) was treated with
pyridine (0.485 mL, 6.00 mmol) and cooled to 0 °C. Dropwise addition of oxalyl
chloride (0.480 mL, 5.50 mmol) was accompanied by vigorous bubbling and conversion
of the clear, colorless solution to a bright yellow and then turbid orange solution. After
stirring at 0 °C for 30 min., dry propylene glycol (0.73 mL, 10.0 mmol) was added in one
portion and the reaction warmed to room temperature.
During this warming phase, the solution changed, first turning orange brown before lightening to yellow. The reaction was diluted with ethanol before being concentrated to an orange brown oil. The oil was
partitioned between 1 N HCl (10 mL) and MtBE (10 mL) and the organic layer washed
with 1 N HCl (2 x 5 mL). The combined aqueous layers were basified with 4 N NaOH to
pH 11, extracted with EtOAc (3 x 40 mL), dried over Na2SO4, filtered, and concentrated
in vacuo.
The oily residue was suspended in Et2O (8 mL) and treated with 1 M HCl in
Et2O (8 mL). This addition formed a lightly colored slurry which was filtered and
washed with Et2O. After drying under vacuum at 50oC for 16 h, 0.66 g of an off-white solid was recovered
decomp. >330 °C.
1H NMR (400 MHz, DMSO-d6)
δ 8.06 (br s, 3H),
2.06 (br s, 3H),
1.77 (m, 6H),
1.59 (m, 6H).
13C NMR (100 MHz, DMSO-d6)
δ 50.8,
40.1,
35.1,
28.2.
Substance data agrees with previously reported information.8
