Tetrahydrofuran → Methyl 1-benzyl-3-(3-bromophenyl)piperidine-4-carboxylate

HRID 1714131ノート

反応式

HRID 1714131 の反応式
C1COCC1.[Br:6][C:7]1[CH:8]=[C:9]([Mg]Br)[CH:10]=[CH:11][CH:12]=1.[CH2:15]([N:22]1[CH2:27][CH:26]=[C:25]([C:28]([O:30][CH3:31])=[O:29])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH2:15]([N:22]1[CH2:27][CH2:26][CH:25]([C:28]([O:30][CH3:31])=[O:29])[CH:24]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([Br:6])[CH:8]=2)[CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 21764251Methyl 1-Benzyl-1,2,3,6-tetrahydropyridine-4-carboxylateHCID 178419620HCID 178419620、化合物

生成物 1

HCID 68504079Methyl 1-benzyl-3-(3-bromophenyl)piperidine-4-carboxylate収率 60.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
20 °C

実験手順

A 0.5 M THF solution of (3-bromophenyl)magnesium bromide (20 mL, 10 mmol) was cooled to −15° C., and methyl 1-benzyl-1,2,3,6-tetrahydropyridine-4-carboxylate (1.05 g, 4.3 mmol) in toluene (3.0 mL) was slowly added for 3 h at −15° C. The reaction mixture was warmed to 20° C. and 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-bromophenyl)piperidine-4-carboxylate (1.0 g, 2.6 mmol).

後処理

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

出典と根拠

ORDレコード
ord-15c39f80fdea4bae98202778e2fd0952
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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