Diisobutylaluminumhydride → tert-Butyl 3-(hydroxymethyl)-3-(4-methylbenzyl)piperidine-1-carboxylate

HRID 1860642노트

반응식

HRID 1860642 반응식
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1[CH:36]=[CH:35][C:15]([CH2:16][C:17]2([C:30](OCC)=[O:31])[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]2)=[CH:14][CH:13]=1>C1COCC1.CCOCC>[OH:31][CH2:30][C:17]1([CH2:16][C:15]2[CH:35]=[CH:36][C:12]([CH3:11])=[CH:13][CH:14]=2)[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:18]1

참가 물질

5

반응물 2

HCID 21225700DiisobutylaluminumhydrideHCID 229784271-Tert-butyl 3-ethyl 3-(4-methylbenzyl)piperidine-1,3-dicarboxylate

생성물 1

HCID 18624164tert-Butyl 3-(hydroxymethyl)-3-(4-methylbenzyl)piperidine-1-carboxylate

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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온도
-20 °C

실험 절차

A solution of diisobutylaluminum hydride (12.0 ml, 12.0 mmol, 1M in THF) was added dropwise to a solution of the product from STEP 2 (1.5 g, 6.0 mmol) in 15 ml THF at −20° C. The resulting mixture was stirred at −20° C. for 20 min and allowed to warm to room temperature. After 3 h, the reaction was diluted with ether (70 ml) and washed with 50 ml of aqueous 1M tartaric acid. The organic extracts were dried with MgSO4, filtered and concentrated. The residue was purified by chromatography (SiO2, ethyl acetate/hexane=1/3) to afford 0.58 g of a viscous. The 1H NMR spectrum of the product was consistent for the proposed structure.

후처리

  1. temperatureto warm to room temperature
  2. waitAfter 3 h
  3. washwashed with 50 ml of aqueous 1M tartaric acid
  4. dry with materialThe organic extracts were dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (SiO2, ethyl acetate/hexane=1/3)
  8. customto afford 0.58 g of a viscous

출처 및 근거

ORD 기록
ord-765d19f4b0b04b8bb67f0a7dd9a7a847
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06531494B1

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