Borane;tetrahydrofuran → HCID 13969852, compound

Temperature

0 °C

N-tert-butoxycarbonyl-D-homophenylalanine (36 mmol) was dissolved in tetrahydrofuran (THF) (300 mL) and cooled to 0° C. Borane-THF complex (0.32 M in THF, 320 mL, 9 equivalents) was added dropwise over 2 hr and the solution stirred for an additional 2 hr at 0° C. The reaction mixture was quenched over several hours by the slow addition of MeOH (300 mL) and the resulting solution was concentrated to dryness. The residue was dissolved in EtOAc (200 mL), washed with 1 N NaOH (2×100 mL) and brine (1×75 mL). The organic layer was dried over Na2SO4, filtered and the filtrate concentrated to dryness. Recrystallization from hexanes gave the title compound (6.5 g, 84%) as a white solid: 1H NMR (CDCl3) δ 1.57 (9H, s), 1.91-1.93 (2H, m), 2.77-2.85 (2H, m), 3.68-3.82 (3H, m), 7.29-7.42 (5H, m); MS m/e 288 (100, M+1).

1. customThe reaction mixture was quenched over several hours by the slow addition of MeOH (300 mL)
2. concentrationthe resulting solution was concentrated to dryness
3. dissolutionThe residue was dissolved in EtOAc (200 mL)
4. washwashed with 1 N NaOH (2×100 mL) and brine (1×75 mL)
5. dry with materialThe organic layer was dried over Na2SO4
6. filtrationfiltered
7. concentrationthe filtrate concentrated to dryness
8. customRecrystallization from hexanes

ORD record

ord-e26dcb271b524ba6b11155ba48e48a5b

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06399629B1