Benzyl Bromide → HCID 22485565, compound

HRID 2181298Notes

Reaction equation

HRID 2181298 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:22])[CH2:9][CH:10]([OH:21])[CH2:11][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[H-].[Na+]>O1CCCC1>[CH2:23]([O:21][CH:10]([CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH3:22])[CH2:11][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH3:13])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 22485464tert-butyl N-(3-{[(tert-butoxy)carbonyl](methyl)amino}-2-hydroxypropyl)-N-methylcarbamate

Product 1

HCID 22485565HCID 22485565, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of N,N′-bis(t-butoxy-carbonyl)-2-hydroxy-N,N′-dimethyl-1,3-propanediamine (87.0 mg, 0.27 mmol) in tetrahydrofuran (4.0 mL) were added benzyl bromide (230.0 mg, 1.35 mmol) and a 50% dispersion of sodium hydride in mineral oil (35.0 mg, 0.81 mmol). The reaction mixture was stirred at room temperature for 15 hours and concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield 2-benzyloxy-N,N′-bis(t-butoxycarbonyl)-N,N′-dimethyl-1,3-propanediamine, obtained as a colorless oil (54.0 mg, yield: 49%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-eb1a69710b704ea891e4fccb6598f8c9
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

Loading…