Diisobutylaluminum hydride → 3-(Dibenzylamino)-2,2-difluoropropan-1-ol

HRID 1365533ノート

反応式

HRID 1365533 の反応式
[CH2:1]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:9][C:10]([F:17])([F:16])[C:11](OCC)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[CH2:18]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]([F:17])([F:16])[CH2:11][OH:12])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 11256065Ethyl 3-(dibenzylamino)-2,2-difluoropropanoate

生成物 1

HCID 589205483-(Dibenzylamino)-2,2-difluoropropan-1-ol収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

At −78° C. to a solution of ethyl 3-(dibenzylamino)-2,2-difluoropropanoate (1.19 g, 3.5 mmol) in THF (20 mL) was added DIBAL-H (15 mL, 1.0 M in hexane, 15 mmol) dropwise. The temperature was maintained at below −70° C. during the addition. After the addition, the acetone-dry ice bath was removed and the reaction mixture was allowed to warm up to room temperature and stirred for 18 h. Celite was added to the reaction mixture, followed by the slow addition of H2O (5 mL), 2 N NaOH (5 mL) and H2O (5 mL). The reaction mixture was filtered, concentrated in vacuo and purified by ISCO chromatography to give 3-(dibenzylamino)-2,2-difluoropropan-1-ol as a colorless oil (810 mg, 80% yield) LCMS: RT=2.48 min [M+H] 292.15 (LCMS Method 1).

後処理

  1. temperatureThe temperature was maintained at below −70° C. during the addition
  2. additionAfter the addition
  3. customthe acetone-dry ice bath was removed
  4. additionCelite was added to the reaction mixture
  5. additionfollowed by the slow addition of H2O (5 mL), 2 N NaOH (5 mL) and H2O (5 mL)
  6. filtrationThe reaction mixture was filtered
  7. concentrationconcentrated in vacuo
  8. custompurified by ISCO chromatography

出典と根拠

ORDレコード
ord-369958fb779b4000beec641ee1507c80
出典データセット
uspto-grants-2011_02
特許番号
US07888376B2

反応ノート

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