Methyl iodide → (1SR,3RS,4SR)-3-cyano-4-methoxy-cyclopentanecarboxylic acid methyl ester

HRID 2244695ノート

反応式

HRID 2244695 の反応式
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([OH:10])[CH:7]([C:11]#[N:12])[CH2:6]1)=[O:4].[CH3:13]I>C1COCC1>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([O:10][CH3:13])[CH:7]([C:11]#[N:12])[CH2:6]1)=[O:4]

参加物

4

反応物 2

HCID 6328Methyl iodideHCID 68685924(1SR,3RS,4SR)-3-cyano-4-hydroxy-cyclopentanecarboxylic acid methyl ester

生成物 1

HCID 68686720(1SR,3RS,4SR)-3-cyano-4-methoxy-cyclopentanecarboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

A solution of (1SR,3RS,4SR)-3-cyano-4-hydroxy-cyclopentanecarboxylic acid methyl ester (878 mg; example 15A) in THF (15 ml) was transferred to a sealed tube and treated with Ag2O (3.6 g) and methyl iodide (3.23 ml) and stirred at 60° C. overnight. The reaction mixture was filtered, and the cake was rinsed with plenty of THF. The filtrate was concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 65:35) to give (1SR,3RS,4SR)-3-cyano-4-methoxy-cyclopentanecarboxylic acid methyl ester (600 mg) as light yellow oil.

後処理

  1. filtrationThe reaction mixture was filtered
  2. washthe cake was rinsed with plenty of THF
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 65:35)

出典と根拠

ORDレコード
ord-0a7b556cfdc34e6f85ae4435ca046022
出典データセット
uspto-grants-2010_03
特許番号
US07678917B2

反応ノート

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