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

HRID 592955ノート

反応式

HRID 592955 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-1a296e01b56e4f8ab9ea7cbb0aa85f17
出典データセット
uspto-grants-2016_01
特許番号
US09238655B2

反応ノート

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