Water → HCID 68916190, compound

HRID 870377Notes

Reaction equation

HRID 870377 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)[CH2:23][CH3:24].O>CN(C)C=O>[C:1]([O:5][C:6](=[O:19])[N: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)[CH2:22][CH2:23][CH3:24])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 68919904HCID 68919904, compound

Product 1

HCID 68916190HCID 68916190, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

((S)-6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester (12.2 g, 37.4 mmol) was dissolved in N,N-dimethylformamide (1000 ml). Sodium hydride (50% in oil) (1.975 g, 41.14 mmol) was added and the mixture was stirred for 15 minutes at room temperature. Propyl bromide (3.74 ml, 41.14 mmol) was added and the reaction mixture was stirred at room temperature over night. The reaction mixture was poured into a mixture of ice and H2O (400 ml) and extracted twice with 200 ml of diethyl ether. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness to yield 14.4 g of crude product. The crude product was purified by chromatography on silica gel using cyclohexane/ethyl acetate (95:5) as eluent, yielding the title compound (10.5 g, 76%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature over night
  2. extractionextracted twice with 200 ml of diethyl ether
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto yield 14.4 g of crude product
  7. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-141bbe352b5d4f22bf3d2f9a1ebfe79f
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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