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

HRID 348978

반응식

HRID 348978 반응식
[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]

참가 물질

5

반응물 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

생성물 1

HCID 21086203Methyl 4-butyl-8-iodo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate수율 91.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ca614a5d2e1e49478c91e8890c8627e2
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

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