Ethanolamine → HCID 15649677, compound

Temperature

65 °C

Dissolve B-(2-(trimethylsilyl)ethynyl)-9-borabicyclo[3.3.1]nonane.tetrahydrofuran complex (2.63 g, 9 mmol) in tetrahydrofuran (30 mL) and add 2- octanone (1.41 mL), 9 mmol). Stir at 65° C. for 48 hours. Cool to room temperature and remove the solvent under a positive nitrogen pressure to give a yellow solid. Add ethyl ether (30 mL) and methanol (365 μL, 9 mmol). Cool to 0° C. and add, by dropwise addition, ethanolamine (543 μL, 9 mmol). Stir overnight, centrifuge the reaction mixture and separate the clear supernatnat liquid. Wash the precipitate with pentane (2×10 mL) and combine the organic phases. Wash with water (2×25 mL) and dry (MgSO4). Evaporate the solvent in vacuo and purify by silica gel chromatography (20:5:1/hexane, chloroform, methanol) to give the title compound as a pale yellow liquid (1.45 g, 71%).

1. temperatureCool to room temperature
2. customremove the solvent under a positive nitrogen pressure
3. customto give a yellow solid
4. temperatureCool to 0° C.
5. stirringStir overnight
6. customcentrifuge the reaction mixture and separate the clear supernatnat liquid
7. washWash the precipitate with pentane (2×10 mL)
8. washWash with water (2×25 mL)
9. dry with materialdry (MgSO4)
10. customEvaporate the solvent in vacuo
11. custompurify by silica gel chromatography (20:5:1/hexane, chloroform, methanol)

ORD record

ord-2fb758a0de544745bb233d2a66fdb38c

Source dataset

uspto-grants-1992_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05157167