Hydrogen Peroxide → 1-(tert-Butyl) 2-methyl 4-(hydroxymethyl)pyrrolidine-1,2-dicarboxylate

HRID 71982

반응식

HRID 71982 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=[CH2:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].[OH2:18].[OH-].[Na+].OO>C1COCC1.C(OCC)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10][OH:18])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

참가 물질

7

반응물 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 592637351-(tert-Butyl) 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate

생성물 1

HCID 235957531-(tert-Butyl) 2-methyl 4-(hydroxymethyl)pyrrolidine-1,2-dicarboxylate수율 41%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

4-Methylene-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (4.48 g, 19.71 mmol) was dissolved in THF (100 mL) and the stirred solution was cooled to 0° C. Borane-dimethylsulfide complex (1.9 mL, 19.7 mmol) was added and the reaction mixture was allowed to warm to RT o/n. After 16 h, water was added dropwise until no bubbling was observed. The stirred mixture was then cooled to 0° C. Aqueous NaOH (5M in H2O, 5.3 mL, 26.6 mmol), then H2O2 (30 wt % in H2O, 6.0 mL, 58.5 mmol) were added dropwise. The reaction was then warmed to 50° C. After 30 min, the mixture was diluted with ethyl ether and washed with water and brine. The organic phase was dried over MgSO4, filtered and concentrated. The crude residue was purified by silica column chromatography (25% to 75% EtOAc/Hex) to afford the title compound (2.08 g, 41%).

후처리

  1. additionBorane-dimethylsulfide complex (1.9 mL, 19.7 mmol) was added
  2. temperatureto warm to RT o/n
  3. temperatureThe stirred mixture was then cooled to 0° C
  4. temperatureThe reaction was then warmed to 50° C
  5. waitAfter 30 min
  6. washwashed with water and brine
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude residue was purified by silica column chromatography (25% to 75% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-adc083c3752642d5bc7464fe75151727
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822430B2

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