Water → tert-Butyl ((5-bromo-1H-pyrrol-3-yl)methyl)(methyl)carbamate

HRID 1962529Notes

Reaction equation

HRID 1962529 reaction equation
[C:1]([O:5][C:6](=[O:25])[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([Br:15])[N:12](S(C2C=CC=CC=2)(=O)=O)[CH:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].O>O1CCCC1.CO.[OH-].[Na+]>[Br:15][C:13]1[NH:12][CH:11]=[C:10]([CH2:9][N:7]([CH3:8])[C:6](=[O:25])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH:14]=1

Participants

6

Reactant 2

HCID 962WaterHCID 66924909tert-butyl{[5-bromo-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate

Product 1

HCID 57522147tert-Butyl ((5-bromo-1H-pyrrol-3-yl)methyl)(methyl)carbamateYield 61%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

tert-Butyl{[5-bromo-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (1.0 g) was dissolved in a mixed solvent of tetrahydrofuran (15 mL) and methanol (5 mL), and 8 mol/L aqueous sodium hydroxide solution (1.5 mL) was added dropwise at not more than 10° C. After stirring at the same temperature for 4 hr, water was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1) to give the title compound as a pale-yellow oil (yield 410 mg, 61%).

Workup

  1. additionwas added dropwise at not more than 10° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1)

Sources & evidence

ORD record
ord-15a775c05f6e465986fadf38a8aaabfc
Source dataset
uspto-grants-2013_04
Patent number
US08415368B2

Reaction notes

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