Sodium hydride → HCID 67429427, compound

HRID 1662784Notes

Reaction equation

HRID 1662784 reaction equation
C([O:8][C:9](=[O:18])[NH:10][C@@H:11]([CH3:17])[C:12]([N:14]([CH3:16])[CH3:15])=[O:13])C1C=CC=CC=1.[H-].[Na+].Br[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:16][N:14]([CH3:15])[C:12](=[O:13])[C@@H:11]([N:10]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)[C:9](=[O:18])[OH:8])[CH3:17]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 5642092-(Bromomethyl)pyridineHCID 69348250Phenylmethyl N-[(1S)-2-(dimethylamino)-1-methyl-2-oxoethyl]carbamate

Product 1

HCID 67429427HCID 67429427, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under nitrogen atmosphere, to a solution of 2.00 g of benzyl[(1S)-2-(dimethylamino)-1-methyl-2-oxo ethyl]carbamate in DMF was added 0.33 g of NaH under ice cooling and the reaction mixture was stirred at room temperature for 10 minutes. Therein, a solution of 3.25 g of 2-(bromo methyl)pyridine in DMF (15 ml) was added, and the solution was stirred at room temperature for 3 hours. A saturated aqueous solution of NaHCO3 was added to the reaction solution, and the resulting mixture was extracted with EtOAc. The combined organic layer was washed with water and with saturated brine and dried over MgSO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60N, moving bed: CHCl3/EtOAc=1/1; v/v) to obtain 1.04 g of the title compound (colorless oil).

Workup

  1. stirringthe solution was stirred at room temperature for 3 hours
  2. extractionthe resulting mixture was extracted with EtOAc
  3. washThe combined organic layer was washed with water and with saturated brine
  4. dry with materialdried over MgSO4
  5. customthe drying agent was separated by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by column chromatography (silicagel 60N, moving bed: CHCl3/EtOAc=1/1; v/v)

Sources & evidence

ORD record
ord-d0548ca44988477a90b5c3ed622cbe1a
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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