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

HRID 473953Notes

Reaction equation

HRID 473953 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-9b2e0014adbe449db1634b351e2ff97b
Source dataset
uspto-grants-2014_01
Patent number
US08637507B2

Reaction notes

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