Water → Allyl-((R)-6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester

HRID 870349Notes

Reaction equation

HRID 870349 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].O>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

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 59747955HCID 59747955, compound

Product 1

HCID 68918871Allyl-((R)-6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl esterYield 73.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

((R)-6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester (3.26 g, 10 mmol) was dissolved in dimethylformamide (30 ml). Sodium hydride (50% in oil) (528 mg, 11 mmol) was added and stirred for 15 minutes at room temperature. Allyl bromide (0.95 ml, 11 mmol) was added and the reaction mixture was stirred at room temperature overnight. To the reaction mixture was added H2O (400 ml) and extracted twice with 150 ml diethylether. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness to yield the crude product (3.25 g). The crude product was purified with silica gel chromatography with cyclohexane/ethyl acetate (9:1) as eluent, yielding the purified product (2.7 g, 66%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. extractionextracted twice with 150 ml diethylether
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto yield the crude product (3.25 g)
  7. customThe crude product was purified with silica gel chromatography with cyclohexane/ethyl acetate (9:1) as eluent

Sources & evidence

ORD record
ord-848e6f10cee840eeae05b7b3ac16bdd4
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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