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Ethyl Acetate → 3-Ethyl-2,3,9,10,11,12-hexahydro-1-methyl-1H-quino[4,3,2-ef][1,4]benzoxazepine fumarate

HRID 981940
ノート
印刷プレビュー

反応式

HRID 981940 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:11]([CH:13]1[C:19](=[O:20])[N:18]([CH3:21])[C:17]2=[C:22]3[C:27](=[N:28][C:29]4=[CH:30][CH:31]=[CH:32][C:15](=[C:16]24)[O:14]1)[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH3:12].[OH-:33].[Na+].[C:35]([O:38]CC)(=[O:37])[CH3:36]>O1CCCC1>[C:19]([OH:20])(=[O:33])/[CH:13]=[CH:36]/[C:35]([OH:38])=[O:37].[CH2:11]([CH:13]1[CH2:19][N:18]([CH3:21])[C:17]2=[C:22]3[C:27](=[N:28][C:29]4=[CH:30][CH:31]=[CH:32][C:15](=[C:16]24)[O:14]1)[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH3:12]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 538029823-ethyl-1,3,9,10,11,12-hexahydro-1-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one

生成物 1

HCID 67756603
3-Ethyl-2,3,9,10,11,12-hexahydro-1-methyl-1H-quino[4,3,2-ef][1,4]benzoxazepine fumarate
収率 38%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of lithium aluminum hydride in tetrahydrofuran (1M, 11.99 ml) and dry tetrahydrofuran (30 ml) was added aluminum chloride (1.6 g) in portions, with stirring. After five mins, 3-ethyl-1,3,9,10,11,12-hexahydro-1-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (3.55 g) was added, and stirring was continued for 0.5 hr. Ethyl acetate (200 ml) and 10% sodium hydroxide solution (200 ml) were added, the organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was flash chromatographed (1.5% triethylamine/toluene). The appropriate fractions were concentrated and the residue was treated with fumaric acid followed by recrystallization from methanol to give 1.82 g (38%) of product, mp 243° C. (dec.).

後処理

  1. stirringstirring
  2. waitwas continued for 0.5 hr
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customchromatographed (1.5% triethylamine/toluene)
  8. concentrationThe appropriate fractions were concentrated
  9. additionthe residue was treated with fumaric acid
  10. customfollowed by recrystallization from methanol

出典と根拠

ORDレコード
ord-76e287b6f2c34491a4397ed20cb2334f
出典データセット
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04994452

反応ノート

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