Allyl bromide → HCID 68913985, compound

HRID 870351Notes

Reaction equation

HRID 870351 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@H:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Br:18])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:22](Br)[CH:23]=[CH2:24]>CN(C)C=O>[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:24][CH:23]=[CH2:22])[C@H:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Br:18])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 68919904HCID 68919904, compound

Product 1

HCID 68913985HCID 68913985, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

((S)-6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester (4.85 g, 14.87 mmol) was dissolved in dimethylformamide (40 ml). Sodium hydride (50% in oil) (785 mg, 16.35 mmol) was added and stirred for 15 minutes at room temperature. Allyl bromide (1.41 ml, 16.35 mmol) was added and the reaction mixture was stirred at room temperature overnight. To the reaction mixture was added H20 (500 ml) and extracted three times with 100 ml diethylether. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness to yield 5.5 g of crude product. The crude product was purified with silica gel chromatography with cyclohexane/ethyl acetate (95:5) as eluent, yielding the purified product (3.9 g, 68%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. additionTo the reaction mixture was added H20 (500 ml)
  3. extractionextracted three times with 100 ml diethylether
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto yield 5.5 g of crude product
  8. customThe crude product was purified with silica gel chromatography with cyclohexane/ethyl acetate (95:5) as eluent

Sources & evidence

ORD record
ord-e891add94999445e9f36b764d066d403
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

Loading…