Dimethyl Sulfide → 1-Benzyl 3-ethyl 3-(2-oxoethyl)piperidine-1,3-dicarboxylate

HRID 2059829ノート

反応式

HRID 2059829 の反応式
[O:1]=[O+][O-].CC(C)=[CH:6][CH2:7][C:8]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:9]1.CSC.C(N(CC)CC)C>C(Cl)Cl>[O:1]=[CH:6][CH2:7][C:8]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:9]1

参加物

6

反応物 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 24823OzoneHCID 598689181-Benzyl 3-ethyl 3-(3-methylbut-2-en-1-yl)piperidine-1,3-dicarboxylate

生成物 1

HCID 598689161-Benzyl 3-ethyl 3-(2-oxoethyl)piperidine-1,3-dicarboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Ozone was passed through a solution of 1-benzyl 3-ethyl 3-(3-methylbut-2-en-1-yl)piperidine-1,3-dicarboxylate (35.2 g, 0.0979 mol) in methylene chloride (800 mL) at −78° C. until the color of the solution turned blue. The reaction mixture was then flushed with nitrogen until the blue color dissipated. Dimethylsulfide (Aldrich, cat #: 274380) (14 mL, 0.19 mol) and triethylamine (26.5 mL, 0.19 mol) were added and the mixture was stirred at ambient temperature overnight. The volatile solvent were removed under reduced pressure and purified directly by flash chromatography on a silica gel column with 20% ethyl acetate in hexanes to afford the desired product in quantitative yield. LC/MS 334.2 (M+H)+.

後処理

  1. customThe reaction mixture was then flushed with nitrogen until the blue color
  2. customThe volatile solvent were removed under reduced pressure
  3. custompurified directly by flash chromatography on a silica gel column with 20% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-e85bc7dc9e3a4c3c9e35283a0a98590f
出典データセット
uspto-grants-2012_10
特許番号
US08278318B2

反応ノート

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