Ethylene Glycol → HCID 178517853、化合物

HRID 1469132ノート

反応式

HRID 1469132 の反応式
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][C@:10]3([CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)[C:9]2=[O:18])[CH2:4][CH2:3]1.[Br:19][C:20]1[CH:25]=[CH:24][C:23](I)=[C:22]([F:27])[CH:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>C(O)CCC.[Cu]I>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([N:14]2[CH2:15][CH2:16][CH2:17][C@@:10]3([C:9](=[O:18])[N:8]([C@H:5]4[CH2:6][CH2:7][C@@H:2]([OH:1])[CH2:3][CH2:4]4)[CH2:12][CH2:11]3)[CH2:13]2)=[C:22]([F:27])[CH:21]=1

参加物

7

反応物 4

HCID 174Ethylene GlycolHCID 62657Potassium Phosphate, TribasicHCID 27245164-Bromo-2-fluoro-1-iodobenzeneHCID 178517863HCID 178517863、化合物

生成物 1

HCID 178517853HCID 178517853、化合物収率 54.2%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 2631-Butanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of (5S)-2-(cis-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one (1.04 g, 0.00412 mol), 4-bromo-2-fluoro-1-iodobenzene (Aldrich, cat #: 283304) (1.85 g, 0.00615 mol), copper(I) iodide (Aldrich, cat #: 215554) (0.122 g, 0.000640 mol), potassium phosphate (2.63 g, 0.0124 mol) and 1,2-ethanediol (0.48 mL, 0.0086 mol) in 1-butanol (3.90 mL) was heated at 100° C. under nitrogen for 2 d. The reaction was quenched with water, and extracted with ether. The organic layers were combined, washed with water, brine, dried over Na2SO4, and filtered. The filtrate was evaporated under reduced pressure. The residue was purified by flash column chromatography on a silica gel column eluting with 0 to 5% methanol in DCM to yield the desired product (950 mg, 54.2%). LC/MS m/e 425.1/427.0 (M+H)+.

後処理

  1. customThe reaction was quenched with water
  2. extractionextracted with ether
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customThe residue was purified by flash column chromatography on a silica gel column
  8. washeluting with 0 to 5% methanol in DCM

出典と根拠

ORDレコード
ord-30ea7a113bae4946bbc2b5a266058af6
出典データセット
uspto-grants-2015_04
特許番号
US09006260B2

反応ノート

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