Tetrahydrofuran → 1-(6-Bromo-2-methylpyridin-3-yl)-2-oxopyrrolidin-3-yl acetate

HRID 705499

반응식

HRID 705499 반응식
Br[CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]([CH3:14])=[N:9][C:10]([Br:13])=[CH:11][CH:12]=2)[C:3]1=[O:15].C1COCC1.[CH3:21][C:22]([O-:24])=[O:23].[K+]>C1OCCOCCOCCOCCOCCOC1.C(OCC)(=O)C>[C:22]([O:24][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]([CH3:14])=[N:9][C:10]([Br:13])=[CH:11][CH:12]=2)[C:3]1=[O:15])(=[O:23])[CH3:21]

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 517044Potassium AcetateHCID 899059653-Bromo-1-(6-bromo-2-methylpyridin-3-yl)pyrrolidin-2-one

생성물 1

HCID 899055871-(6-Bromo-2-methylpyridin-3-yl)-2-oxopyrrolidin-3-yl acetate수율 65%

시약·촉매·용매 2

HCID 2855718-Crown-6촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

A 500 mL round-bottom flask was charged with crude 3-bromo-1-(6-bromo-2-methylpyridin-3-yl)pyrrolidin-2-one from step A (18.5 g), THF (50 mL), 18-Crown-6 (576 mg, 2.18 mmol) and KOAc (12.84 g, 131 mmol). The mixture was heated at 70° C. under argon overnight. After cooling the reaction mixture to room temperature, ethyl acetate (50 mL) was added. The organic layer was separated and washed with water (50 mL), brine (50 mL), dried over MgSO4, filtered and concentrated to a dark solid, which was purified by flash chromatography (silica gel, 20-100% ethyl acetate/hexane) to give 1-(6-bromo-2-methylpyridin-3-yl)-2-oxopyrrolidin-3-yl acetate (8.9 g, 65% yield for two steps) as white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.38 (q, J=8.3 Hz, 3H), 5.43 (t, J=8.2 Hz, 1H), 3.47-4.03 (m, 3H), 2.62-2.90 (m, 1H), 2.38-2.56 (m, 4H), 2.06-2.32 (m, 5H); MS (ESI) 314 (M+H).

후처리

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. customThe organic layer was separated
  3. washwashed with water (50 mL), brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a dark solid, which
  7. customwas purified by flash chromatography (silica gel, 20-100% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-e8ba83085ec043ac92cb45a36c825e95
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174965B2

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