1-Methylpiperidine-2,3-dione → 3-Ethynyl-3-hydroxy-1-methylpiperidin-2-one

HRID 1398525ノート

反応式

HRID 1398525 の反応式
[C:1]([Mg]Br)#[CH:2].[CH3:5][N:6]1[CH2:11][CH2:10][CH2:9][C:8](=[O:12])[C:7]1=[O:13]>O1CCCC1>[C:1]([C:8]1([OH:12])[CH2:9][CH2:10][CH2:11][N:6]([CH3:5])[C:7]1=[O:13])#[CH:2]

参加物

4

反応物 2

HCID 126685381-Methylpiperidine-2,3-dioneHCID 178418486HCID 178418486、化合物

生成物 1

HCID 866695763-Ethynyl-3-hydroxy-1-methylpiperidin-2-one収率 30%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethynylmagnesium bromide (0.5M in tetrahydrofuran, 4 mL, 2 mmol) maintained under nitrogen at −20° C. was added a solution of 1-methylpiperidine-2,3-dione (220 mg, 0.87 mmol) in tetrahydrofuran (3 mL) dropwise with stirring within 1 min. The reaction mixture was stirred for 2 hr at room temperature and then quenched by the addition of saturated ammonium chloride solution (1 mL). The mixture was diluted with DCM (50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The crude residue was purified on a silica gel column, elution with ethyl acetate/petroleum ether (0:1-1:0) afforded the title compound (40 mg, 30%) as a brown oil: 1H NMR (400 MHz, CDCl3) delta 4.23 (s, 1H), 3.35-3.30 (m, 2H), 2.95 (s, 3H), 2.47 (s, 1H), 2.35-2.16 (m, 2H), 1.97-1.90 (m, 2H). LC-MS m/z=+154 [M+H]+.

後処理

  1. stirringThe reaction mixture was stirred for 2 hr at room temperature
  2. customquenched by the addition of saturated ammonium chloride solution (1 mL)
  3. additionThe mixture was diluted with DCM (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude residue was purified on a silica gel column, elution with ethyl acetate/petroleum ether (0:1-1:0)

出典と根拠

ORDレコード
ord-d2dd33afe9514108a8274f70d20b3479
出典データセット
uspto-grants-2014_12
特許番号
US08901313B2

反応ノート

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