Dimethyl Sulfoxide → (2S)-5-allyloxycarbonylimino-2-formyl-1-methylpyrrolidine

HRID 1090526ノート

反応式

HRID 1090526 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:14][C:15]([N:17]=[C:18]1[N:22]([CH3:23])[C@H:21]([CH2:24][OH:25])[CH2:20][CH2:19]1)=[O:16])[CH:12]=[CH2:13].C(N(CC)CC)C>ClCCl>[CH2:11]([O:14][C:15]([N:17]=[C:18]1[N:22]([CH3:23])[C@H:21]([CH:24]=[O:25])[CH2:20][CH2:19]1)=[O:16])[CH:12]=[CH2:13]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57267024(2S)-5-allyloxycarbonylimino-2-hydroxymethyl-1-methylpyrrolidine

生成物 1

HCID 57243365(2S)-5-allyloxycarbonylimino-2-formyl-1-methylpyrrolidine収率 73.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of oxalyl chloride (0.52 ml) in dichloromethane (15 ml) was added dropwise dimethyl sulfoxide (0.60 ml) at -78° C. After stirring at -78° C. for 10 minutes, to the mixture was added dropwise a solution of (2S)-5-allyloxycarbonylimino-2-hydroxymethyl-1-methylpyrrolidine (0.63 g) in dichloromethane (10 ml). After stirring at -78° C. for 10 minutes, to the mixture was added dropwise triethylamine (2.1 ml) and the resulting mixture was allowed to warm to 0° C. The mixture was washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of acetone and dichloromethane (1:4 V/V) to give (2S)-5-allyloxycarbonylimino-2-formyl-1-methylpyrrolidine (0.46 g).

後処理

  1. stirringAfter stirring at -78° C. for 10 minutes, to the mixture
  2. temperatureto warm to 0° C
  3. washThe mixture was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel eluting with a mixture of acetone and dichloromethane (1:4 V/V)

出典と根拠

ORDレコード
ord-d76dbee60845478f9e5664e5935736af
出典データセット
uspto-grants-1992_01
特許番号
US05081237

反応ノート

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