(2S)-(Methylamino)(phenyl)acetic acid → (S)-2-(Methylamino)-2-phenylethanol

To a suspension of LiAlH4 (0.689 g, 18.16 mmol) in THF (20.18 mL) was added (S)-2-(methylamino)-2-phenylacetic acid (1 g, 6.05 mmol) in THF (20 mL) slowly over 10 min at 0° C. The reaction mixture was stirred at room temperature for overnight. After quenched with water (0.7 mL), NaOH (2.1 mL), water (0.7 mL). The reaction mixture was filtered off. The filtrate was extracted with EtOAc 3 times. The combined organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered off, and concentrated in vacuo. The crude product was purified by flash chromatography (10% methanol in DCM) yielding (S)-2-(methylamino)-2-phenylethanol as a colorless oil in 55% yield. LCMS (m/z): 152.1 (MH+), 0.31 min; 1H NMR (400 MHz, CDCl3) δ7.40-7.33 (m, 2H), 7.32-7.27 (m, 3H), 3.77-3.69 (m, 1H), 3.69-3.63 (m, 1H), 3.58 (d, J=9.8 Hz, 1H), 2.36 (s, 3H).

1. customAfter quenched with water (0.7 mL), NaOH (2.1 mL), water (0.7 mL)
2. filtrationThe reaction mixture was filtered off
3. extractionThe filtrate was extracted with EtOAc 3 times
4. washThe combined organic layer was washed with water and brine
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered off
7. concentrationconcentrated in vacuo
8. customThe crude product was purified by flash chromatography (10% methanol in DCM)

ORD record

ord-90b51c5f4bee437b9b88568f646d8b79

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242996B2