1-Aminocyclohexanecarboxylic acid → (1-Aminocyclohexyl)methanol

Temperature

0 °C

LiAlH4 powder (2.28 g, 60.0 mmol) was placed in a 200 mL round-bottom flask equipped with a magnetic stir bar. The flask was evacuated and backflushed with Ar, cooled to 0° C., and charged with dry THF (10 mL) via cannula. 1-Amino-cyclohexylcarboxylic acid (2.86 g, 20.0 mmol) was added in small portions as a solid. Upon completion of the addition, the mixture was heated to reflux for 12 h. The mixture was cooled to 0° C., treated slowly with satd aq Na2 CO3 (50 mL), warmed to rt, and stirred for 2 h. A white precipitate formed, which was separated by filtration, washed with THF (75 mL), and washed twice with EtOAc (100 mL). The filtrate was concentrated in vacuo. The residue was dissolved in DCM (50 mL), dried over Na2 SO4, and concentrated in vacuo to afford 2.80 g (97%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 3.33 (s, 2H), 1.45-1.56 (m, 6H), 1.31-1.45 (m, 4H).

1. customequipped with a magnetic stir bar
2. customThe flask was evacuated
3. additioncharged with dry THF (10 mL) via cannula
4. additionUpon completion of the addition
5. temperaturethe mixture was heated
6. temperatureto reflux for 12 h
7. temperatureThe mixture was cooled to 0° C.
8. additiontreated slowly with satd aq
9. customA white precipitate formed
10. customwhich was separated by filtration
11. washwashed with THF (75 mL)
12. washwashed twice with EtOAc (100 mL)
13. concentrationThe filtrate was concentrated in vacuo
14. dissolutionThe residue was dissolved in DCM (50 mL)
15. customdried over Na2 SO4
16. concentrationconcentrated in vacuo

ORD record

ord-35b6360b935c436181ab844e717ec20b

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232409B2