Acetyl chloride → (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride
Reaktionsgleichung
C([Cl:4])(=O)C.[OH:5][C@H:6]1[C@H:11]([CH3:12])[CH2:10][CH2:9][C@@H:8]([NH:13]C(=O)OC(C)(C)C)[CH2:7]1>CO>[ClH:4].[NH2:13][C@H:8]1[CH2:7][C@@H:6]([OH:5])[C@H:11]([CH3:12])[CH2:10][CH2:9]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To vigorously stirring methanol (149 mL) at 0° C. was added acetyl chloride (15.87 mL, 223 mmol) and the resulting mixture stirred for 10 min. To this solution was added tert-butyl (1R,3R,4R)-3-hydroxy-4-methylcyclohexylcarbamate (17.08 g, 74.5 mmol) and the mixture was stirred for 22 h at room temperature. The crude reaction was concentrated and then triturated with ethyl ether (2×300 mL) to afford (1R,2R,5R)-5-amino-2-methylcyclohexanol hydrochloride (12.2 g, 73.6 mmol, 99% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.02 (br. s., 3H), 4.77 (d, J=5.86 Hz, 1H), 2.85-3.10 (m, 2H), 2.03-2.21 (m, 1H), 1.83 (d, J=11.71 Hz, 1H), 1.65 (dd, J=13.47, 3.32 Hz, 1H), 1.24 (q, J=11.58 Hz, 2H), 1.12 (dd, J=6.05, 3.32 Hz, 1H), 0.82-1.03 (m, 4H).