(2S,3S)-2,3-dihydroxy-N,N,N',N'-tetramethylbutanediamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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)+. as reported in Organic Synthesis, 1998, 76, 86-96 The two layers were separated the aqueous layer was extracted with dichloromethane (30 mL) The combined organic layers were washed with brine dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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)+. as reported in Organic Synthesis, 1998, 76, 86-96 The two layers were separated the aqueous layer was extracted with dichloromethane (30 mL) The combined organic layers were washed with brine dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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)+. as reported in Organic Synthesis, 1998, 76, 86-96 The two layers were separated the aqueous layer was extracted with dichloromethane (30 mL) The combined organic layers were washed with brine dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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)+. as reported in Organic Synthesis, 1998, 76, 86-96 The two layers were separated the aqueous layer was extracted with dichloromethane (30 mL) The combined organic layers were washed with brine dried over MgSO4 filtered concentrated in vacuo