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

HRID 705499

反応式

HRID 705499 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 2855718-Crown-6触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e8ba83085ec043ac92cb45a36c825e95
出典データセット
uspto-grants-2015_11
特許番号
US09174965B2

関連ノート

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