(2S)-2-amino-2-cyclopentylacetic acid → (2S)-2-Amino-2-cyclopentylethan-1-ol

To a stirred solution of (S)-2-amino-2-cyclopentylacetic acid (1.00 g, 6.98 mmol) in THF (20 mL) was added dropwise a solution of LiAlH4 in THF (1.0 M, 10.5 mL, 10.5 mmol) at 0° C. under N2. The reaction was allowed to warm to ambient temperature and heated at reflux overnight. After cooling, the reaction mixture was cooled to 0° C. and carefully quenched by dropwise addition of water (0.4 mL) followed by 15% NaOH solution (0.4 mL) and water (1.2 mL). The mixture was stirred at ambient temperature for 15 minutes and filtered through Celite. The filtrate was concentrated to give crude (S)-2-amino-2-cyclopentylethanol, which was used in the next step without further purification.

1. temperatureheated
2. temperatureat reflux overnight
3. temperatureAfter cooling
4. temperaturethe reaction mixture was cooled to 0° C.
5. customcarefully quenched by dropwise addition of water (0.4 mL)
6. filtrationfiltered through Celite
7. concentrationThe filtrate was concentrated

ORD record

ord-3cb664679bbe4c53b79f6abc3bd5c2e2

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865726B2