Borane;tetrahydrofuran → HCID 13969852, compound

Temperature

0 °C

N-tert-butoxycarbonyl-D-homophenylalanine (36 mmol) was dissolved in THF (300 mL) and cooled to 0° C. Borane-THF complex (0.32M in THF, 320 mL, 9 equivalents) was added dropwise over 2 hours and the solution was stirred for an additional 2 hours at 0° C. The reaction mixture was quenched over several hours by the slow addition of MeOH (300 mL) and the 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 NASO4, filtered and the filtrate concentrated to dryness. Recrystallization from hexanes gave the title compound (6.5g, 84%) as a white solid: 1H NMR (400 MHz, 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 (5)H, m); MS (relative intensity) nme 288 (100, M+1).

1. customThe reaction mixture was quenched over several hours by the slow addition of MeOH (300 mL)
2. concentrationthe 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. customThe organic layer was dried over NASO4
6. filtrationfiltered
7. concentrationthe filtrate concentrated to dryness
8. customRecrystallization from hexanes

ORD record

ord-30f0527e68b44fee838665f399f0de4e

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06399629B1