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

HRID 1411892노트

반응식

HRID 1411892 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1c3933633e46496c87dd75e0641b258e
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921353B2

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