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

HRID 73296

Reaktionsgleichung

Reaktionsgleichung von HRID 73296
[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.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]

Komponenten

6

Edukt 3

HCID 8113DiethanolamineHCID 20479Butylboronic AcidHCID 6610750N,N,N',N'-Tetramethyl-L-tartramide

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

2-(But-1-yl)-tetrahydro-4H-1,3,6,2-dioxazaborocine [CAS 92527-13-4] (3 g, 17.5 mmol), which 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, and (2R,3R)-2,3-dihydroxy-N,N,N′,N′-tetramethyl-butanediamide [CAS 26549-65-5] (9.85 g) were dissolved in anhydrous dichloromethane (160 mL) under N2, Brine (25 mL) was added. The resulting mixture was stirred at room temperature for about 16 hours. The two layers were separated, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with 50 mL brine, dried over MgSO4, filtered and concentrated in vacuo to provide the title compound as an oil.

Aufarbeitung

  1. customThe two layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with 50 mL brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5e1ec3aea6574a1d88a733e20de2ceb7
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829041B2

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