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

HRID 1860642ノート

反応式

HRID 1860642 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-765d19f4b0b04b8bb67f0a7dd9a7a847
出典データセット
uspto-grants-2003_03
特許番号
US06531494B1

反応ノート

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