Sodium Hydroxide → 1669402-65-6

To a solution of N-(2-phenyl-2-(S)-hydroxyethyl)-4-(2-aminoethyl)aniline trifluoroacetate 31 (0.144 g, 0.3 mmole) in methanol (10 mL) was added aq. NaOH solution (1.0 M, 0.625 mL). The solution was concentrated to dryness and the residue was dissolved in anhydrous THF (5 mL). α,α-Dihydroxy-4-hydroxy-3-methoxycarbonylacetophenone 12 (0.067 g, 0.3 mmole) was added and the reaction mixture was stirred for 12 h at rt. BH3-Me2S (0.2 mL, 2 M) was added at 0° C. and the reaction mixture was heated at 75° C. for 6 h. After cooling the reaction mixture in ice bath, MeOH (5 mL) was slowly added to it to quench the reaction, and the reaction mixture was stirred for 30 min., at rt. The organics were removed and the residue was dissolved in TFA/MeOH (1/9; 20 mL), and concentrated. The crude product was dissolved in 20% MeCN/H2O, and purified by preparative HPLC: 5 to 20% MeCN/H2O; 20 mL/min; 254 nm.) to give 1-{2-[N-2-(4-hydroxy-3-hydroxymethylphenyl)-2-hydroxyethyl]amino]ethyl}-4-[N-(2-phenyl-2-(S)-hydroxyethyl)-amino]benzene 33.

1. concentrationThe solution was concentrated to dryness
2. dissolutionthe residue was dissolved in anhydrous THF (5 mL)
3. temperaturethe reaction mixture was heated at 75° C. for 6 h
4. temperatureAfter cooling the reaction mixture in ice bath
5. customto quench
6. customthe reaction
7. stirringthe reaction mixture was stirred for 30 min., at rt
8. customThe organics were removed
9. dissolutionthe residue was dissolved in TFA/MeOH (1/9; 20 mL)
10. concentrationconcentrated
11. dissolutionThe crude product was dissolved in 20% MeCN/H2O
12. custompurified by preparative HPLC

ORD record

ord-dc800b93f0e24fcab864b9e6cb911e2e

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06916961B2