Ethyl bromoacetate → HCID 68112906, Verbindung

(1R,2S)-2-amino-1,2-diphenylethanol (2.10 g) was dissolved in dichloromethane (30 ml) and stirred at room temperature. Ethyl bromoacetate (2.00 g), dissolved in dichloromethane (15 ml), was added to the solution. The mixture was stirred at room temperature for 7 days, and then triethylamine (1.5 ml) was added and stirred at room temperature for an additional day. After the spot of the starting material in TLC disappeared, dichloromethane was evaporated under reduced pressure Benzene (100 ml) was added to the remaining residue, and the triethylamine hydrobromide salt was washed out with water. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solution was filtered and evaporated. The residue (2.60 g, 88%) was recrystallized from hexane (ca. 300 ml). The crystals deposited were collected and dried under reduced pressure. Yield 2.20 g (75%); mp 123-125° C.; [α]D18 +2.4° (c 1.00, EtOH). IR (KBr): 3180, 1745, 765, 705 cm- 1. 1H-NMR (CDC13): 1.17 (t, 3H, J =7 Hz), 2.35 (bs, 2H), 3.16 (pseudo s, 2H), 3.98 (q, 2H, J =7 Hz), 4.15 (d, 1H, J =6 Hz), 4.76 (d, 1H, J =6 Hz), 7.20 (s, 10H) ppm.

1. additionwas added to the solution
2. stirringThe mixture was stirred at room temperature for 7 days
3. stirringstirred at room temperature for an additional day
4. customdichloromethane was evaporated under reduced pressure Benzene (100 ml)
5. additionwas added to the remaining residue
6. washthe triethylamine hydrobromide salt was washed out with water
7. washThe organic layer was washed with brine
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationThe solution was filtered
10. customevaporated
11. customThe residue (2.60 g, 88%) was recrystallized from hexane (ca. 300 ml)
12. customThe crystals deposited were collected
13. customdried under reduced pressure

ORD-Eintrag

ord-92910a4899024fcb8da2169aa11e6c87

Quelldatensatz

uspto-grants-1990_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04966985