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

HRID 1714140노트

반응식

HRID 1714140 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

반응 조건

온도
-15 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bcede513a1d44b43b9027d3e1b14246d
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795436B2

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