Benzyl Bromide → HCID 67230052, compound

HRID 1511908Notes

Reaction equation

HRID 1511908 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:15])[NH:9][N:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)([CH3:6])([CH3:5])[CH3:4].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[C:3]([O:7][C:8](=[O:15])[N:9]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[N:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 49760548tert-Butyl 1H-pyrrol-1-ylcarbamate

Product 1

HCID 67230052HCID 67230052, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (313 mg, 7.83 mmol, 60% purity in mineral oil) was added in one portion to a stirred, ice/water-cooled solution of pyrrol-1-yl-carbamic acid tert-butyl ester (951 mg, 5.22 mmol) and benzyl bromide (745 μL, 6.26 mmol) in DMF (20 mL); the mixture was stirred in the cold bath for 30 min, at which time TLC showed complete disappearance of starting material; then poured into diluted, cold ammonium chloride solution to quench the reaction, followed by extraction with EtOAc, then washed with water, and brine; then the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, and the residue was silica gel column purified to give desired product (1.376 g) as a clear oil. ESI (m/z): 273 (M+H)+.

Workup

  1. additionthen poured
  2. additioninto diluted
  3. customcold ammonium chloride solution to quench
  4. customthe reaction
  5. extractionfollowed by extraction with EtOAc
  6. washwashed with water, and brine
  7. dry with materialthen the organic phase was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified

Sources & evidence

ORD record
ord-6acba77bd147480ebc67a32b601dbdfa
Source dataset
uspto-grants-2012_07
Patent number
US08217043B2

Reaction notes

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