Methyl iodide → HCID 67296619、化合物

HRID 1969373ノート

反応式

HRID 1969373 の反応式
[H-].[Na+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH2:10][C@H:11]1[NH:15][C:14](=[O:16])[CH2:13][CH2:12]1.[CH3:17]I>CN(C=O)C>[CH3:17][N:15]1[C@H:11]([CH2:10][O:9][CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][O:3]2)[CH2:12][CH2:13][C:14]1=[O:16]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10878146HCID 10878146、化合物

生成物 1

HCID 67296619HCID 67296619、化合物収率 92.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
-40 °C

実験手順

To a mixture of NaH (0.48 g, 12 mmol, 60% mineral oil, Aldrich) in 15 mL of DMF was added a solution of (S)-5-((tetrahydro-2H-pyran-2-yloxy)methyl)pyrrolidin-2-one (2 g, 10 mmol) in 5 mL of DMF via a syringe at −40° C. The reaction was stirred at −40° C. for 1 hr. CH3I (0.9 mL, 12 mmol, Shanghai Jingchun Reagent Ltd.) was added dropwise via a syringe. The reaction was continued to stir at −40° C. for 4 hrs, and was quenched with 10 mL of saturated NaHSO3 aqueous solution. The mixture was extracted with ethyl acetate (50 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc) to give the desired product as colorless oil (1.98 g, 92%).

後処理

  1. stirringto stir at −40° C. for 4 hrs
  2. customwas quenched with 10 mL of saturated NaHSO3 aqueous solution
  3. extractionThe mixture was extracted with ethyl acetate (50 mL×3)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (EtOAc)

出典と根拠

ORDレコード
ord-ecdee3bd935b4778b815c092b5db3737
出典データセット
uspto-grants-2013_04
特許番号
US08426585B2

反応ノート

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