Diisopropyl diazene-1,2-dicarboxylate → Methyl 3-(5-bromopyridin-2-yloxy)cyclopentane carboxylate

HRID 473953

反応式

HRID 473953 の反応式
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3]1.[Br:11][C:12]1[CH:13]=[CH:14][C:15](O)=[N:16][CH:17]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([O:1][CH:2]2[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3]2)=[N:16][CH:17]=1

参加物

5

反応物 3

HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 520596Cyclopentanecarboxylic acid, 3-hydroxy-, methyl esterHCID 178515818HCID 178515818、化合物

生成物 1

HCID 58577907Methyl 3-(5-bromopyridin-2-yloxy)cyclopentane carboxylate収率 51%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

A solution of methyl 3-hydroxycyclopentanecarboxylate A-11 (500.0 mg, 3.00 mmol) in anhydrous toluene (10.0 mL) was added to a solution of 5-bromopyridin-2-ol (522.0 mg, 3.00 mmol) in anhydrous toluene (10.0 mL) at room temperature. Diisopropyl azodicarboxylate (1.57 g, 6.00 mmol) was then added dropwise, and the yellow-orange solution was stirred at room temperature for 12 h. The reaction mixture was then quenched with methanol (1.0 mL) and concentrated to dryness under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexanes to ethyl acetate gradient) to give methyl 3-(5-bromopyridin-2-yloxy)cyclopentane carboxylate A-12 (462.0 mg, Yield=51%). MS (ESI), [M+Na]+ 321, 323.

後処理

  1. customThe reaction mixture was then quenched with methanol (1.0 mL)
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe residue was purified by flash column chromatography on silica gel (hexanes to ethyl acetate gradient)

出典と根拠

ORDレコード
ord-9b2e0014adbe449db1634b351e2ff97b
出典データセット
uspto-grants-2014_01
特許番号
US08637507B2

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