Diethanolamine → 2-Butyl-1,3,6,2-dioxazaborocane

2-(But-1-yl)-tetrahydro-4H-1,3,6,2-dioxazaborocine [CAS 92527-13-4] was prepared from n-butylboronic acid and 2-(2-hydroxy-ethylamino)-ethanol [CAS 111-42-2] as reported in Organic Synthesis, 1998, 76, 86-96. This dioxazaborocine (3 g, 17.5 mmol) and (2S,3S)-2,3-dihydroxy-N,N,N′,N′-tetramethyl-butanediamide [CAS 63126-52-3] (4.65 g) were dissolved in anhydrous dichloromethane (95 mL) under N2. Brine (30 mL) was added. The resulting mixture was stirred at room temperature for 1 hour. The two layers were separated, and the aqueous layer was extracted with dichloromethane (30 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide the title compound as an oil. 1H NMR (300 MHz, CDCl3): δ 0.82-0.9 (m, 5H), 1.25-1.45 (m, 4H), 2.98 (s, 6H), 3.2 (s, 6H), 5.52 (s, 2H). MS (DCl—NH3) m/z 271 (M+H)+.

1. customas reported in Organic Synthesis, 1998, 76, 86-96
2. customThe two layers were separated
3. extractionthe aqueous layer was extracted with dichloromethane (30 mL)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-86f1dfbdfa4246fe81e2e8f61fc969c5

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108948B2