Aluminum(III) Chloride → 2,3,9,10,11,12-Hexahydro-1-methyl-1H-quino-[4,3,2-ef][1,4]benzoxazepine

HRID 1195766노트

반응식

HRID 1195766 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:11][N:12]1[C:18]2=[C:19]3[C:24](=[N:25][C:26]4=[CH:27][CH:28]=[CH:29][C:16](=[C:17]24)[O:15][CH2:14][C:13]1=O)[CH2:23][CH2:22][CH2:21][CH2:20]3>O1CCCC1>[CH3:11][N:12]1[C:18]2=[C:19]3[C:24](=[N:25][C:26]4=[CH:27][CH:28]=[CH:29][C:16](=[C:17]24)[O:15][CH2:14][CH2:13]1)[CH2:23][CH2:22][CH2:21][CH2:20]3

참가 물질

5

반응물 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 53993904HCID 53993904, 화합물

생성물 1

HCID 538157592,3,9,10,11,12-Hexahydro-1-methyl-1H-quino-[4,3,2-ef][1,4]benzoxazepine수율 89.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of lithium aluminum hydride in tetrahydrofuran (1.0M, 15.82 ml) and dry tetrahydrofuran (32 ml) was added aluminum chloride (2.10 g) in portions. The mixture was stirred for five mins, 1,3,9,10,11,12-hexahydro-1-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.24 g) was added and the mixture was stirred at room temperature overnight. The reaction mixture was quenched with ethyl acetate (150 ml), 10% sodium hydroxide solution was added, and the organic layer was separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was adhered to silica (methanol) and flash chromatographed (30-50% ethyl acetate/Hexane) to yield 3.61 g (89.6%) of product, mp 97°-98° C.

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe reaction mixture was quenched with ethyl acetate (150 ml), 10% sodium hydroxide solution
  3. additionwas added
  4. customthe organic layer was separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed (30-50% ethyl acetate/Hexane)

출처 및 근거

ORD 기록
ord-95cbb7a7668f4708afa754da845cd9a0
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05112829

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