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

HRID 473953

반응식

HRID 473953 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9b2e0014adbe449db1634b351e2ff97b
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637507B2

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