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

HRID 1365533노트

반응식

HRID 1365533 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-369958fb779b4000beec641ee1507c80
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888376B2

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