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

HRID 1714131노트

반응식

HRID 1714131 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
20 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-15c39f80fdea4bae98202778e2fd0952
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795436B2

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