(S)-2,2-dimethyl-4-((E)-2-phenyl-propenyl)-oxazolidine-3-carboxylic acid tert-butyl ester → (S)-2-amino-4-phenyl-pentan-1-ol

A solution of (S)-2,2-dimethyl-4-((E)-2-phenyl-propenyl)-oxazolidine-3-carboxylic acid tert-butyl ester (700 mg) in EtOH (30 ml) and CHCl3 (15 ml) was treated with 10% Pd/C (200 mg) and hydrogenated with a balloon overnight. The catalyst was filtered off, washed with EtOH and concentrated. The residue was dissolved in EtOH (10 ml) and treated with 2N HCl (15 ml). The mixture was heated for 90 min to 100° C., then concentrated. The residue was taken up in 1N NaOH and extracted with CH2Cl2/MeOH 4:1. The organic layer was dried over MgSO4, filtrated and concentrated. The crude product was purified by column chromatography (SiO2; gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give (S)-2-amino-4-phenyl-pentan-1-ol (342 mg) as off-white waxy solid.

1. filtrationThe catalyst was filtered off
2. washwashed with EtOH
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in EtOH (10 ml)
5. additiontreated with 2N HCl (15 ml)
6. temperatureThe mixture was heated for 90 min to 100° C.
7. concentrationconcentrated
8. extractionextracted with CH2Cl2/MeOH 4:1
9. dry with materialThe organic layer was dried over MgSO4
10. filtrationfiltrated
11. concentrationconcentrated
12. customThe crude product was purified by column chromatography (SiO2; gradient: CH2Cl2->CH2Cl2/MeOH 9:1)

ORD record

ord-9f813112bb934ecb833b4a889f1be558

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604061B2