1-Benzyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate → 1-Benzyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate

HRID 1864915

반응식

HRID 1864915 반응식
[CH2:1]([C:4]1([C:20]([O:22][CH3:23])=[O:21])[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1)[CH:2]=C.C1C=C[NH+]=CC=1.[O-:30][Cr](Cl)(=O)=O>C1COCC1.C(Cl)Cl.CCOCC>[O:30]=[CH:2][CH2:1][C:4]1([C:20]([O:22][CH3:23])=[O:21])[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[CH2:6][CH2:5]1

참가 물질

6

반응물 2

HCID 588931861-Benzyl 4-methyl 4-allylpiperidine-1,4-dicarboxylateHCID 178418287HCID 178418287, 화합물

생성물 1

HCID 588931821-Benzyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 1-benzyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate from Step B (4.45 g, 14.0 mmol) in THF (70 mL) at 0° C. was added borane-methyl sulfide complex (28.0 mL of a 2M solution in THF, 56.1 mmol). The reaction mixture was slowly warmed to ambient temperature and stirred for 16 h, then quenched with water and concentrated in vacuo. The residue was dissolved in CH2Cl2 (140 mL) and added drop wise to a solution of PCC (6.65 g. 30.8 mmol) and 4 Å molecular sieves (6.65 g) in CH2Cl2 (50 mL) at 0° C. The reaction mixture was warmed to ambient temperature and stirred for 16 h, then diluted with ether (200 mL) and filtered through a pad of celite. Additional ether was used to wash the celite. The combined organics were concentrated in vacuo to give a residue that was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH-100:0 to 95:5, to give the title compound. MS: m/z=356 (M+Na).

후처리

  1. customquenched with water
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (140 mL)
  4. temperatureThe reaction mixture was warmed to ambient temperature
  5. stirringstirred for 16 h
  6. filtrationfiltered through a pad of celite
  7. washto wash the celite
  8. concentrationThe combined organics were concentrated in vacuo
  9. customto give a residue that
  10. customwas purified by silica gel chromatography
  11. washeluting with a gradient of CH2Cl2

출처 및 근거

ORD 기록
ord-9495b06a2b7f47d689f4fb3ebd02d74b
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625901B2

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