Tetrahydrofuran → HCID 40425511, compound

Temperature

20 °C

T a solution of (R)-3-amino-3-(3,4-dichlorophenyl)propanoic acid (10.0 g, 42.7 mmol, CASRN 909709-44-0) and THF (57.0 mL, 42.7 mmol) under a N2 atmosphere and cooled to 0° C. was added dropwise LiAlH4 (32.0 mL, 32.0 mmol, 1M solution in THF) at a rate that maintained the internal temperature at 20° C. (10 min addition). The reaction was stirred at 0° C. for 1 h, then warmed to RT and stirred overnight. The reaction was quenched with 2M HCl (20 mL) then 2M NaOH (30 mL) and brine (50 mL) were added sequentially. The white solids were removed by filtration through CELITE and rinsed with THF (100 mL) and EtOAc (50 mL). The organic phase was dried (Na2SO4), filtered and concentrated to afford 5.25 g (56%) of (R)-3-amino-3-(3,4-dichlorophenyl)propan-1-ol (172) as a light yellow oil which was used without additional purification: MS m/z (APCI-pos) M+1=220.0.

1. addition(10 min addition)
2. temperaturewarmed to RT
3. stirringstirred overnight
4. customThe reaction was quenched with 2M HCl (20 mL)
5. addition2M NaOH (30 mL) and brine (50 mL) were added sequentially
6. customThe white solids were removed by filtration through CELITE
7. washrinsed with THF (100 mL) and EtOAc (50 mL)
8. dry with materialThe organic phase was dried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-2a6c6c6ca12f4b1c96f60031b379d5d6

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133187B2