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

HRID 515041

반응식

HRID 515041 반응식
[CH2:1]([B:5]([OH:7])[OH:6])[CH2:2][CH2:3][CH3:4].O[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]O.O1C=CC=CB=NO1.O[C@@H]([C@H](O)C(N(C)C)=O)C(N(C)C)=O>ClCCl.[Cl-].[Na+].O>[CH2:1]([B:5]1[O:7][CH2:13][CH2:12][NH:11][CH2:10][CH2:9][O:6]1)[CH2:2][CH2:3][CH3:4]

참가 물질

7

반응물 4

HCID 8113DiethanolamineHCID 20479Butylboronic AcidHCID 69992572,3-Dihydroxy-N~1~,N~1~,N~4~,N~4~-tetramethylbutanediamideHCID 57497284Dioxazaborocin

생성물 1

HCID 3466072-Butyl-1,3,6,2-dioxazaborocane

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-86f1dfbdfa4246fe81e2e8f61fc969c5
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108948B2

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