Methanol → Methyl 3-aminoadamantane-1-carboxylate hydrochloride

温度

60 °C

To a 3-neck 2-L flask equipped with a reflux condenser and a temperature probe was added 3-amino-adamantane-1-carboxylic acid hydrochloride (100 g, 432 mmol) and methanol (1.0 L). To this solution was slowly added thionyl chloride (15.7 mL, 216 mmol) and the reaction was heated at 60° C. for 4 hours. Once cooled to room temperature, the crude reaction mixture was concentrated under reduced pressure to remove most of the methanol. Heptane (about 1-L) was then added and the mixture was once again concentrated under reduced pressure at which point a solid began to precipitate. This process was repeated three more times, then the solids were filtered off, washed with heptane and allowed to dry in open air to afford 97.2 g (92%) of the title compound, 3-amino-adamantane-1-carboxylic acid methyl ester hydrochloride, as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.46 (br s, 3H), 3.65 (s, 3H), 2.33-2.24 (m, 2H), 2.23-2.16 (m, 2H), 2.11-1.95 (m, 4H), 1.94-1.78 (m, 4H), 1.75-1.62 (m, 2H).

1. temperatureOnce cooled to room temperature
2. customthe crude reaction mixture
3. concentrationwas concentrated under reduced pressure
4. customto remove most of the methanol
5. additionHeptane (about 1-L) was then added
6. concentrationthe mixture was once again concentrated under reduced pressure at which point a solid
7. customto precipitate
8. filtrationthe solids were filtered off
9. washwashed with heptane
10. customto dry in open air

ORDレコード

ord-17b0c007efe2480b9f075217e90e3ac2

出典データセット

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08389519B2