1-Adamantanecarboxylic acid → Tricyclo(3.3.1.13,7)decane-1-carboxamide

반응식

[C:1]12([C:11]([OH:13])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C1N=C[N:16](C(N2C=NC=C2)=O)C=1.[NH4+].[OH-]>CCOC(C)=O>[C:1]12([C:11]([NH2:16])=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

참가 물질

실험 절차

A solution of adamantane-1-carboxylic acid (2.00 g, 11.10 mmol) in EtOAc (20 mL) was treated with CDI (2.00 g, 12.33 mmol), stirred at RT for 20 minutes, treated with NH4OH (˜14M, 5 mL, ˜70 mmol) and stirred at RT for 20 minutes. The mixture was concentrated to dryness, treated with satd. NaHCO3 and the solids collected via filtration and dried to afford adamantane-1-carboxamide (1.74 g, 87%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.91 (s, 1H), 6.65 (s, 1H), 1.92 (m, 3H), 1.74-1.71 (m, 6H), 1.68-1.57 (m, 6H); MS (ESI) m/z: 180.1 (M+H+).