Propargyl alcohol → HCID 178463301、化合物

HRID 1469158ノート

反応式

HRID 1469158 の反応式
Br[C:2]1[CH:3]=[C:4]([N:13]([C@H:16]2[CH2:21][CH2:20][C@H:19]([N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH3:23])[CH2:18][CH2:17]2)[CH2:14][CH3:15])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(NC(C)C)(C)C.[CH2:38]([OH:41])[C:39]#[CH:40]>C1(C)C=CC=CC=1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:27]([O:26][C:24]([N:22]([CH3:23])[C@H:19]1[CH2:20][CH2:21][C@H:16]([N:13]([CH2:14][CH3:15])[C:4]2[C:5]([CH3:12])=[C:6]([CH:11]=[C:2]([C:40]#[C:39][CH2:38][OH:41])[CH:3]=2)[C:7]([O:9][CH3:10])=[O:8])[CH2:17][CH2:18]1)=[O:25])([CH3:28])([CH3:29])[CH3:30]

参加物

8

反応物 3

HCID 7859Propargyl alcoholHCID 7912DiisopropylamineHCID 178463214HCID 178463214、化合物

生成物 1

HCID 178463301HCID 178463301、化合物収率 63.2%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)(methyl)amino)cyclohexyl)(ethyl)amino)-2-methylbenzoate (2 g, 4.14 mmol) in dry toluene was added CuI (0.015 g, 0.079 mmol), PPh3 (0.043 g, 0.165 mmol), PdCl2(PPh3)2 (0.058 g, 0.082 mmol), N,N-diisopropyl amine (1.08 g, 10.78 mmol) and reaction was purged with argon for 15 min. prop-2-yn-1-ol (0.46 g, 8.29 mmol) was added to it reaction was heated at 80° C. at sealed condition for 5 h. On completion, it was quenched with water and extracted with ethyl acetate. Organic layer was dried over Na2SO4. The crude compound was purified by column chromatography to afford the title compound (1.2 g, 63.2% yield).

後処理

  1. additionwas added to it reaction
  2. customat sealed condition for 5 h
  3. customOn completion, it was quenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialOrganic layer was dried over Na2SO4
  6. customThe crude compound was purified by column chromatography

出典と根拠

ORDレコード
ord-f9d00b1007a84423b0fdc450db2300a1
出典データセット
uspto-grants-2015_04
特許番号
US09006242B2

反応ノート

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