1,2-Dibromoethane → Tert-butyl 4-(4-bromobenzyl)-4-hydroxypiperidine-1-carboxylate

HRID 60575

反応式

HRID 60575 の反応式
[Mg].BrCCBr.[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Br)=[CH:9][CH:8]=1.[O:15]=[C:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1.[Cl-].[NH4+]>C(OCC)C>[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][C:16]2([OH:15])[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:20][CH2:21]2)=[CH:9][CH:8]=1

参加物

7

反応物 5

HCID 78391,2-DibromoethaneHCID 25517Ammonium ChlorideHCID 685274-Bromobenzyl bromideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5462224Magnesium

生成物 1

HCID 70851437Tert-butyl 4-(4-bromobenzyl)-4-hydroxypiperidine-1-carboxylate収率 40.4%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒3 回

実験手順

To a suspension of magnesium (2.9 g) in diethyl ether (50 mL) was added dropwise 1,2-dibromoethane (0.90 mL) at room temperature, and the reaction mixture was vigorously stirred at room temperature for 20 min. To the reaction mixture was added dropwise a solution of 4-bromobenzyl bromide (25 g) in diethyl ether (150 mL) over 30 min or more at 0° C., and then added dropwise a solution of tert-butyl 4-oxopiperidine-1-carboxylate (16 g) in diethyl ether (200 mL) over 30 min or more 0° C. The reaction mixture was allowed to warm to room temperature, and stirred at room temperature for 3 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution (200 mL), and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (12 g).

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred at room temperature for 3 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-dba157cd4aee4c5faa3e18ea51cfbaaf
出典データセット
uspto-grants-2016_09
特許番号
US09440990B2

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