Hydrochloric Acid → 3-(Isopropylamino)azetidine-3-carboxamide hydrochloride

Participants

Reaction Steps

To a solution of 1-benzhydryl-3-isopropylaminoazetidine-3-carboxylic acid amide (I-(7A-106)b; 2.28 g, 7.05 mmol) in methanol (100 ml) was added 1M HCl in ether (14.8 ml, 14.8 mmol) and then water (10 ml). After the addition of 20% Pd(OH)2 on carbon (60% water; 1.43 g), the mixture was placed on a Parr® shaker and then reduced (50 psi H2) at room temperature overnight. The mixture was filtered through a pad of Celite®, and then concentrated, in vacuo. The residue was then concentrated, in vacuo, from toluene (2×), acetonitrile (2×) and then methanol to give I-(7A-106)c (1.59 g, 98%) as a tan solid: +ACPI MS (M+1) 158.1; 1H NMR (400 MHz, CD3OD) δ 4.71 (d, J=13.3 Hz, 2H), 4.60 (d, J=13.3 Hz, 2H), 3.49 (septuplet, J=6.6 Hz, 1H), 1.34 (d, J=6.6 Hz, 6H).

Provenance & Evidence