Water → HCID 68916190, compound

HRID 870388Notes

Reaction equation

HRID 870388 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 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 overnight. The reaction mixture was poured into a mixture of ice and H2O (400 ml) and twice extracted with 200 ml 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 with silica gel chromatography with cyclohexane/ethyl acetate (95:5) as eluent, yielding the purified product (10.5 g, 76%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. extractiontwice extracted with 200 ml 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 with silica gel chromatography with cyclohexane/ethyl acetate (95:5) as eluent

Sources & evidence

ORD record
ord-bb4d7495509b447d8bbd291abf060374
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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