Ethanolamine → Methyl 4-butyl-8-iodo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

HRID 14187

Reaktionsgleichung

Reaktionsgleichung von HRID 14187
[CH2:1]([N:5]1[C:10]2[CH:11]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[C:14]([I:15])[C:9]=2[O:8][CH2:7][C:6]1=O)[CH2:2][CH2:3][CH3:4].B1C2CCCC1CCC2.C(CN)O>O1CCCC1>[CH2:1]([N:5]1[C:10]2[CH:11]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[C:14]([I:15])[C:9]=2[O:8][CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 700EthanolamineHCID 789669-Borabicyclo(3.3.1)nonaneHCID 21086204Methyl 4-butyl-8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

Produkt 1

HCID 21086203Methyl 4-butyl-8-iodo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylateAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of Methyl 4-butyl-8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (680 mg) and 9-BBN (900 mg) in tetrahydrofuran (30 mL) was heated at reflux for 1.5 h. The mixture was cooled to room temperature, ethanolamine (0.22 mL) was added, and the resulting solution was concentrated under reduced pressure. The residue was washed with hexanes, filtered, and the filtrate was concentrated under reduced pressure. Purification by flash column chromatography (silica, 10% ethyl acetate/hexanes) afforded 600 mg of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.75, 7.28, 4.34, 3.86, 3.36, 3.28, 1.58, 1.40, 0.96.

Aufarbeitung

  1. temperatureat reflux for 1.5 h
  2. concentrationthe resulting solution was concentrated under reduced pressure
  3. washThe residue was washed with hexanes
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customPurification by flash column chromatography (silica, 10% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6c64bd91ce79480595b00e36b5437384
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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