HCID 9795992, 화합물 → HCID 57672014, 화합물

HRID 657611노트

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HRID 657611 반응식
[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]

참가 물질

4

반응물 2

HCID 9795992HCID 9795992, 화합물HCID 178418573HCID 178418573, 화합물

생성물 1

HCID 57672014HCID 57672014, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-41bfa7b5a2e843e49697c89efef1525e
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076329B2

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