Cyclohexene → HCID 57822475, compound

A solution of cyclohexene (8.5 mL, 84 mmol) and borane dimethylsulfide (10.5 mL, 105 mmol) in dry ether (90 mL) at 0° C. was stirred for 3 h. The solvent was removed by syringe, and the precipitate was washed with ether. The precipitate was suspended in THF (50 mL) and a solution of benzyl prop-2-yn-1-ylcarbamate (7.912 g, 41.8 mmol) in THF (50 mL) was added at 0° C. The resulting mixture was stirred at rt for 1 hr. To the mixture was added trimethylamine N-oxide dihydrate (13.94 g, 125 mmol) and the mixture was stirred at rt for 16 hr. The mixture was quenched with 2N HCl. The organic layer was separated and the aqueous layer was extracted with ether. The combined organic layers were extracted three times with 10% aqueous NaOH. The combined aqueous layers were washed with ether and made acidic with 2N HCl to give (E)-(3-(((benzyloxy)carbonyl)amino)prop-1-en-1-yl)boronic acid as a precipitate that was filtered and air dried to white solid (2.38 g, 24%). The material was used without purification.

1. customThe solvent was removed by syringe
2. washthe precipitate was washed with ether
3. stirringthe mixture was stirred at rt for 16 hr
4. customThe mixture was quenched with 2N HCl
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with ether
7. extractionThe combined organic layers were extracted three times with 10% aqueous NaOH
8. washThe combined aqueous layers were washed with ether

ORD record

ord-838542ac87d14af4b38a8deec69329ab

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765767B2