Aluminium lithium hydride → 2,3,4,5-Tetrahydro-8-(trifluoromethyl)-1H-1,4-benzodiazepine

HRID 2246999ノート

反応式

HRID 2246999 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][C:6]2[C:7](=O)[NH:8][CH2:9][C:10](=O)[NH:11][C:5]=2[CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:15]=[CH:14][C:6]2[CH2:7][NH:8][CH2:9][CH2:10][NH:11][C:5]=2[CH:4]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydride2 回HCID 21904835HCID 21904835、化合物

生成物 1

HCID 219048172,3,4,5-Tetrahydro-8-(trifluoromethyl)-1H-1,4-benzodiazepine収率 69.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
68 °C

実験手順

To a solution of 8-(trifluoromethyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (1.5 g, 6.1 mmol) in THF (1 mL) at room temperature was added lithium aluminum hydride in THF (28 mL, 28 mmol) over 10 minutes. Once the addition was completed, the reaction was heated to 68° C. After 24 hours, additional lithium aluminum hydride in THF was added (12.3 mmol) over five minutes. After 3 hours, the reaction mixture was cooled to 0° C., and then quenched with water, 15% NaOH, and an additional portion of water. After filtering off the gray precipitate and rinsing with ethyl acetate, the solvent was removed from the filtrate. The resulting solid was then redissolved in ethyl acetate and transferred to a separatory funnel and washed with water (3×), dried with magnesium sulfate, filtered and concentrated to give a yellow solid. Further purification (15% ammonia in 2M solution of ethanol/ethyl acetate) yielded 0.918 g of desired product (69%).

後処理

  1. additionOnce the addition
  2. waitAfter 3 hours
  3. temperaturethe reaction mixture was cooled to 0° C.
  4. customquenched with water, 15% NaOH
  5. filtrationAfter filtering off the gray precipitate
  6. washrinsing with ethyl acetate
  7. customthe solvent was removed from the filtrate
  8. dissolutionThe resulting solid was then redissolved in ethyl acetate
  9. customtransferred to a separatory funnel
  10. washwashed with water (3×)
  11. dry with materialdried with magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customto give a yellow solid
  15. customFurther purification (15% ammonia in 2M solution of ethanol/ethyl acetate)

出典と根拠

ORDレコード
ord-0c1a0594e0f848c28e5fc146d8bc5f87
出典データセット
uspto-grants-2010_03
特許番号
US07687620B2

反応ノート

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