HCID 9795992、化合物 → HCID 57672014、化合物

HRID 657611ノート

反応式

HRID 657611 の反応式
[C:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][C@@H:16]([CH3:18])[CH2:15][C@H:14]([CH3:19])[CH2:13]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:22][Mg]Br>O1CCCC1>[OH:3][C:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][C@@H:14]([CH3:19])[CH2:15][C@H:16]([CH3:18])[CH2:17]2)=[CH:6][CH:5]=1)([CH3:22])[CH3:2]

参加物

4

反応物 2

HCID 9795992HCID 9795992、化合物HCID 178418573HCID 178418573、化合物

生成物 1

HCID 57672014HCID 57672014、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of trans-1-[3-(4-acetylphenoxy)propyl]-3,5-dimethylpiperidine (289 mg) in tetrahydrofuran (1 mL) is stirred at room temperature under anhydrous atmosphere and a 2.61 M solution of methylmagnesium bromide in tetrahydrofuran (400 μL) is added dropwise. The mixture is stirred at room temperature for 3 h and quenched with a saturated aqueous solution of ammonium chloride. The solution is extracted with ethyl acetate and the combined extracts washed with water, dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel with dichloro-methane/methanol 95/5 as eluent. Fractions containing the expected product are pooled and salted with 20 mg of oxalic acid to give 70 mg of trans-1-{3-[4-(1-hydroxy-1-methylethyl)-phenoxy]propyl}-3,5-dimethylpiperidine, oxalate as a pale yellow solid.

後処理

  1. customquenched with a saturated aqueous solution of ammonium chloride
  2. extractionThe solution is extracted with ethyl acetate
  3. washthe combined extracts washed with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by chromatography over silica gel with dichloro-methane/methanol 95/5 as eluent
  7. additionFractions containing the expected product

出典と根拠

ORDレコード
ord-41bfa7b5a2e843e49697c89efef1525e
出典データセット
uspto-grants-2011_12
特許番号
US08076329B2

反応ノート

読み込み中…