Diisobutylaluminum hydride → 2-Methyl-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)propanal

HRID 1848554노트

반응식

HRID 1848554 반응식
[CH3:1][C:2]([N:9]1[CH2:19][CH2:18][C:12]2([C:16](=[O:17])[NH:15][CH2:14][CH2:13]2)[CH2:11][CH2:10]1)([CH3:8])[C:3](OCC)=[O:4].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH3:8][C:2]([N:9]1[CH2:19][CH2:18][C:12]2([C:16](=[O:17])[NH:15][CH2:14][CH2:13]2)[CH2:11][CH2:10]1)([CH3:1])[CH:3]=[O:4]

참가 물질

4

반응물 2

HCID 14487Diisobutylaluminum hydrideHCID 86709536Ethyl 2-methyl-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)propanoate

생성물 1

HCID 867095372-Methyl-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)propanal

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of ethyl 2-methyl-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)propanoate (3.77 g, 14.1 mmol) in toluene (100 mL) at −78° C. was added DIBAL-H (45.0 mL, 45.0 mmol) dropwise. After 2 h, the reaction was quenched by addition of methanol (10 mL) dropwise, after warmed to rt, 30 mL of saturated sodium sulfate solution was added and the mixture was vigorously stirred at rt for 1 h. After filtration, the filtrate and the filter cake were partitioned between DCM and saturated sodium bicarbonate, the alkaline phase was extracted with DCM three times, the combined organic phase was dried over sodium sulfate, concentrated to give the title compound. LC/MS (M+1+18)+: 243.3; (M+1+32)+: 257.4.

후처리

  1. customthe reaction was quenched by addition of methanol (10 mL) dropwise
  2. addition30 mL of saturated sodium sulfate solution was added
  3. filtrationAfter filtration
  4. customthe filtrate and the filter cake were partitioned between DCM and saturated sodium bicarbonate
  5. extractionthe alkaline phase was extracted with DCM three times
  6. dry with materialthe combined organic phase was dried over sodium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ca6c5b579abc4513a7f9b098cb2039d0
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952166B2

반응 노트

불러오는 중…