Triethylamine → (1-pyrrolidin-1-ylindan-5-yl)propynoic Acid

HRID 735030

反応式

HRID 735030 の反応式
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:6][CH2:5]2.[C:16]([OH:20])(=[O:19])[C:17]#[CH:18].C(N(CC)CC)C>C(#N)C.[Cu]I>[N:11]1([CH:7]2[C:8]3[C:4](=[CH:3][C:2]([C:18]#[C:17][C:16]([OH:20])=[O:19])=[CH:10][CH:9]=3)[CH2:5][CH2:6]2)[CH2:15][CH2:14][CH2:13][CH2:12]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 10110Propiolic AcidHCID 688183461-(5-Iodoindan-1-yl)pyrrolidine

生成物 1

HCID 68817830(1-pyrrolidin-1-ylindan-5-yl)propynoic Acid

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6342Acetonitrile溶媒

実験手順

Under an argon atmosphere at 0° C., 0.5 g (1.59 mmol) of 1-(5-iodoindan-1-yl)pyrrolidine and 123 mL (2 mmol) of propynoic acid are dissolved in 25 mL of acetonitrile. 0.66 mL (4.79 mmol) of triethylamine, 30 mg (0.16 mmol) of copper (I) iodide, and 80 mg (0.11 mmol) of ditriphenylphosphine palladium dichloride are added to this solution and the mixture is stirred for 2 hours, while the solution is allowed to come up to ambient temperature. The purification is carried out by preparative HPLC (eluant: dichloromethane/methanol/ammonia (8:2:0.2)). Yield 0.1 g (24.5% of theory); C16H17NO2 (M=255.31); calc.: molecular ion peak (M+H)+: 256; found: molecular ion peak (M+H)+: 256.

後処理

  1. customto come up to ambient temperature
  2. customThe purification

出典と根拠

ORDレコード
ord-ea9c97f40edd4f55833fa381371bd748
出典データセット
uspto-grants-2009_09
特許番号
US07592373B2

関連ノート

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