Bis(2-bromoethyl) ether → 1352306-49-0

Bis(2-bromoethyl)ether (2.3 g, 10 mmol) was added to (5)-2-aminopropan-1-ol (3.8 g, 50 mmol) at room temperature with vigorous stirring. The reaction slowly exothermed and the internal temperature peaked at 42° C. after 19 min. After 24 h, the reaction was diluted with dichloromethane (10 mL) and quenched with saturated aqueous potassium carbonate solution (10 mL). Water (˜2.5 mL) was added to the heterogeneous mixture until the solids dissolved. The layers were separated, and the aqueous layer was extracted with dichloromethane (2×10 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated under reduced pressure to afford the crude product. The crude material was purified by silica gel chromatography (10:7; ethyl acetate:hexanes→10:7:2:1; ethyl acetate:hexanes:methanol:triethylamine) to give 1.27 g of (S)-2-morpholinopropan-1-ol. 1H NMR (DMSO-d6): δ 4.29 (dd, 1H), 3.54 (t, 4H), 3.45 (ddd, 1H), 3.25 (ddd, 1H), 2.54-2.40 (m, 5H), 0.92 (d, 3H); LCMS: 146.1 (M+H)+.

1. customThe reaction
2. waitAfter 24 h
3. customquenched with saturated aqueous potassium carbonate solution (10 mL)
4. additionWater (˜2.5 mL) was added to the heterogeneous mixture until the solids
5. dissolutiondissolved
6. customThe layers were separated
7. extractionthe aqueous layer was extracted with dichloromethane (2×10 mL)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customto afford the crude product
12. customThe crude material was purified by silica gel chromatography (10:7; ethyl acetate:hexanes→10:7:2:1; ethyl acetate:hexanes:methanol:triethylamine)

ORD record

ord-d1b92f840bc84db1a9bdaf2c9c3c43b5

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187460B2