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

HRID 1866717

反応式

HRID 1866717 の反応式
[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

参加物

6

反応物 2

HCID 588931861-Benzyl 4-methyl 4-allylpiperidine-1,4-dicarboxylateHCID 178418287HCID 178418287、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d274b83117b6417eb66aee2063d88151
出典データセット
uspto-grants-2009_12
特許番号
US07629338B2

関連ノート

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