1-Bromopropane → HCID 67071015, compound

HRID 2357011Notes

Reaction equation

HRID 2357011 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Br:17])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:21](Br)[CH2:22][CH3:23]>CN(C)C=O>[C:1]([O:5][C:6](=[O:18])[N:7]([C@H:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Br:17])[CH:14]=2)[CH2:9]1)[CH2:21][CH2:22][CH3:23])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 78401-Bromopropane2×HCID 24758Sodium hydride2×HCID 67071021HCID 67071021, compound

Product 1

HCID 67071015HCID 67071015, compoundYield 110.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3 g of ((R)-5-Bromo-indan-2-yl)-carbamic acid tert-butyl ester (9.61 mmol) were dissolved in 20 ml of dimethylformamide and 0.442 g of sodium hydride (60% in mineral oil) (11.05 mmol) added. Stirring continued for 14 minutes before 1.3 g of propylbromide (10.57 mmol) were added. The reaction mixture was stirred at room temperature for 15 h and at 40° C. for 3 h. An additional equivalent of sodium hydride and 0.7 ml propylbromide were added followed by stirring for 2 h at 40° C. and 15 h at room temperature. The solvent was evaporated under reduced pressure, the residue treated with water and extracted three times with diethyl ether. The combined organic layers were washed once with water, dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to yield 3.77 g of crude product which was used in the subsequent reaction without further purification.

Workup

  1. additionwere added
  2. stirringThe reaction mixture was stirred at room temperature for 15 h and at 40° C. for 3 h
  3. stirringby stirring for 2 h at 40° C. and 15 h at room temperature
  4. customThe solvent was evaporated under reduced pressure
  5. additionthe residue treated with water
  6. extractionextracted three times with diethyl ether
  7. washThe combined organic layers were washed once with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-35c30493742247aaa6961d8fa0e7ef52
Source dataset
uspto-grants-2010_07
Patent number
US07759397B2

Reaction notes

Loading…