Tetrahydrofuran → HCID 40425511, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence