Methyl 1-Benzyl-1,2,3,6-tetrahydropyridine-4-carboxylate → Methyl 1-benzyl-3-(3-bromo5-methyl-phenyl)piperidine-4-carboxylate

HRID 1714140ノート

反応式

HRID 1714140 の反応式
C1COCC1.C1(C)C=CC=CC=1.[Br:13][C:14]1[CH:15]=[C:16]([Mg]Br)[CH:17]=[C:18]([CH3:20])[CH:19]=1.[CH2:23]([N:30]1[CH2:35][CH:34]=[C:33]([C:36]([O:38][CH3:39])=[O:37])[CH2:32][CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1C=CC=CC=1>[CH2:23]([N:30]1[CH2:31][CH2:32][CH:33]([C:36]([O:38][CH3:39])=[O:37])[CH:34]([C:16]2[CH:17]=[C:18]([CH3:20])[CH:19]=[C:14]([Br:13])[CH:15]=2)[CH2:35]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

参加物

5

反応物 3

HCID 21764251Methyl 1-Benzyl-1,2,3,6-tetrahydropyridine-4-carboxylateHCID 22635083Tetrahydrofuran tolueneHCID 178422449HCID 178422449、化合物

生成物 1

HCID 68501586Methyl 1-benzyl-3-(3-bromo5-methyl-phenyl)piperidine-4-carboxylate収率 71.1%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
-15 °C

実験手順

A 2.5 M THF/toluene solution of (3-bromo-5-methylphenyl)magnesium bromide (40 mL, 99 mmol) was cooled to −15° C., and methyl 1-benzyl-1,2,3,6-tetrahydropyridine-4-carboxylate (9.85 g, 42.6 mmol) in benzene (17.5 mL) was slowly added for 3 h at −15° C. The reaction mixture was stirred additional 2 h at −15° C. and warmed to 20° C. The reaction was quenched by addition of saturated NH4Cl aqueous solution followed by extraction with EtOAc. The combined organic solution was dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed in silica gel column (Hex/EtOAc 9/1) to give methyl 1-benzyl-3-(3-bromo5-methyl-phenyl)piperidine-4-carboxylate (12.2 g, 30.3 mmol).

後処理

  1. temperaturewarmed to 20° C
  2. customThe reaction was quenched by addition of saturated NH4Cl aqueous solution
  3. extractionfollowed by extraction with EtOAc
  4. dry with materialThe combined organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed in silica gel column (Hex/EtOAc 9/1)

出典と根拠

ORDレコード
ord-bcede513a1d44b43b9027d3e1b14246d
出典データセット
uspto-grants-2010_09
特許番号
US07795436B2

反応ノート

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