Potassium bisulfate → methyl 3-[(E)-tert-butylsulfinyliminomethyl]-5,6,7,8-tetrahydroindolizine-2-carboxylate

HRID 1022024ノート

反応式

HRID 1022024 の反応式
[CH:1]([C:3]1[N:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)=[CH:5][C:4]=1[C:12]([O:14][CH3:15])=[O:13])=O.[CH3:16][C:17]([S:20]([NH2:22])=[O:21])([CH3:19])[CH3:18].OS([O-])(=O)=O.[K+]>ClCCl>[C:17]([S:20](/[N:22]=[CH:1]/[C:3]1[N:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)=[CH:5][C:4]=1[C:12]([O:14][CH3:15])=[O:13])=[O:21])([CH3:19])([CH3:18])[CH3:16]

参加物

5

反応物 3

HCID 516920Potassium bisulfateHCID 3382465Tert-ButanesulfinamideHCID 86683769Methyl 3-formyl-5,6,7,8-tetrahydroindolizine-2-carboxylate

生成物 1

HCID 89548949methyl 3-[(E)-tert-butylsulfinyliminomethyl]-5,6,7,8-tetrahydroindolizine-2-carboxylate収率 83%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A 500-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with methyl 3-formyl-5,6,7,8-tetrahydroindolizine-2-carboxylate (10.0 g, 48.3 mmol, 1.0 eq.), 2-methylpropane-2-sulfinamide (11.7 g, 96.6 mmol, 2.0 eq.), KHSO4 (32.8 g, 241.5 mmol, 5 eq.), and dichloromethane (250 mL). The mixture was stirred at room temperature for 10 h. It was then filtered and filtrate was concentrated under reduced pressure. The resulting residue was purified by silica-gel column chromatography eluting with 1:3 ethyl acetate/petroleum ether to afford 238a (12.4 g, 83%) as a yellow solid. MS: [M+H]+ 311.3.

後処理

  1. customA 500-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. filtrationIt was then filtered
  3. concentrationfiltrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica-gel column chromatography
  5. washeluting with 1:3 ethyl acetate/petroleum ether

出典と根拠

ORDレコード
ord-430718f7a7dc45329072d2b0b8076f04
出典データセット
uspto-grants-2014_05
特許番号
US08716274B2

反応ノート

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