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

HRID 349008

반응식

HRID 349008 반응식
[CH2:1]([N:5]1[C:10]2[CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=[CH:14][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:15]([O:17][CH3:18])=[O:16])[CH:13]=[CH:14][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 21086200Methyl 4-butyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

생성물 1

HCID 21086198Methyl 4-butyl-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate수율 80.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of methyl 4-butyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (800 mg) and 9-BBN (1.6 g) in tetrahydrofuran (13 mL) was refluxed for 1.5 h. The mixture was cooled to room temperature, ethanolamine (0.4 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, 25% ethyl acetate/hexanes) afforded 607 mg of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 7.21, 7.16, 6.75, 4.24–4.21, 3.78, 3.34–3.24, 1.55–1.47, 1.38–1.30, 0.95–0.90.

후처리

  1. concentrationthe resulting solution was concentrated under reduced pressure
  2. washThe residue was washed with hexanes
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customPurification by flash column chromatography (silica, 25% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-95f9ca50e434407a8f6c89eeb4c2978d
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

연결된 노트

불러오는 중…