2-Amino-2-phenylpropanoic acid → 2-Amino-2-phenylpropan-1-ol

To a stirred, cooled suspension of 2-amino-2-phenyl-propionic acid (488 mg) at r.t. in THF (10 ml) under an argon atmosphere was added portionwise LiAlH4 (244 mg). The ice bath was removed and stirring at r.t. was then continued for 20 h. The mixture was cooled in an ice bath, diluted with 5 ml THF and H2O (0.23 ml), 4 N NaOH (0.23 ml) and H2O (0.92 ml) were added successively and carefully. After 30 min stirring at r.t., the mixture was filtered and the cake was washed with THF. The filtrate was concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give 2-amino-2-phenyl-propan-1-ol (266 mg) as colorless viscous oil. MS (ISP): 152.3 ([M+H]+)

1. temperatureTo a stirred, cooled
2. customThe ice bath was removed
3. temperatureThe mixture was cooled in an ice bath
4. additiondiluted with 5 ml THF and H2O (0.23 ml), 4 N NaOH (0.23 ml) and H2O (0.92 ml)
5. additionwere added successively
6. stirringAfter 30 min stirring at r.t.
7. filtrationthe mixture was filtered
8. washthe cake was washed with THF
9. concentrationThe filtrate was concentrated
10. customThe crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1)

ORD record

ord-8017bd5b09104673b8972ec110dafeee

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604061B2