Sodium hydride → 4-(4-Bromo-7-methoxybenzofuran-2-ylmethoxy)-piperidine-1-carboxylic Acid tert-butyl Ester

HRID 1108319Notes

Reaction equation

HRID 1108319 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[Br:17][C:18]1[C:23]2[CH:24]=[C:25]([CH2:27]Br)[O:26][C:22]=2[C:21]([O:29][CH3:30])=[CH:20][CH:19]=1>CN(C)C=O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([O:16][CH2:27][C:25]2[O:26][C:22]3[C:21]([O:29][CH3:30])=[CH:20][CH:19]=[C:18]([Br:17])[C:23]=3[CH:24]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 187848624-Bromo-2-bromomethyl-7-methoxybenzofuran

Product 1

HCID 540770204-(4-Bromo-7-methoxybenzofuran-2-ylmethoxy)-piperidine-1-carboxylic Acid tert-butyl EsterYield 37.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (72 mg of a 60% dispersion in oil) was added to a stirred solution of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (363 mg) in N,N-dimethylformamide (10 ml) under an inert atmosphere at ambient temperature. After stirring for 30 minutes 4-bromo-2-bromomethyl-7-methoxybenzofuran (526 mg) was added and the reaction stirred overnight. The reaction mixture was preadsorbed onto silica and purified by column chromatography eluting with 25% ethyl acetate in hexane to afford the desired product as a yellow oily solid (269 mg).

Workup

  1. additionwas added
  2. custompurified by column chromatography
  3. washeluting with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a0a6e6304ee54ba0aca4296cf35656ee
Source dataset
uspto-grants-2000_05
Patent number
US06066657

Reaction notes

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