Sodium borohydride → HCID 66782618, compound

HRID 1095449Notes

Reaction equation

HRID 1095449 reaction equation
[BH4-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([C:15]1[N:19]([CH2:20][C:21](OCC)=[O:22])[CH:18]=[N:17][CH:16]=1)=[CH:10][CH2:9][CH2:8]2)#[N:4]>C(O)C>[OH:22][CH2:21][CH2:20][N:19]1[C:15]([C:11]2[C:12]3[CH:13]=[CH:14][C:5]([C:3]#[N:4])=[CH:6][C:7]=3[CH2:8][CH2:9][CH:10]=2)=[CH:16][N:17]=[CH:18]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86632963HCID 86632963, compound

Product 1

HCID 66782618HCID 66782618, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

43.0 mmol of sodium borohydride are added in portions to a solution of 19.5 mmol of ethyl [5-(6-cyano-3,4-dihydronaphthalen-1-yl)imidazol-1-yl]acetate in 150 ml of ethanol at 0° C. The reaction mixture is stirred at room temperature for 2 hours and then evaporated. The residue is taken up in saturated aqueous sodium bicarbonate solution, and dichloromethane is added to the mixture. The reaction mixture is stirred at room temperature for 10 minutes and the phases are separated. The aqueous phase is back-extracted with dichloromethane, and the combined organic phases are washed with brine, dried with sodium sulphate and evaporated. The title compound is obtained as a white solid from the residue by flash chromatography (SiO2 60F). Rf=0.16 (dichloromethane-methanol-25% aqueous ammonia solution 200:20:1); Rt=5.04 (gradient II).

Workup

  1. customevaporated
  2. additiondichloromethane is added to the mixture
  3. stirringThe reaction mixture is stirred at room temperature for 10 minutes
  4. customthe phases are separated
  5. extractionThe aqueous phase is back-extracted with dichloromethane
  6. washthe combined organic phases are washed with brine
  7. dry with materialdried with sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-83927282d49748e4809d17764aef4505
Source dataset
uspto-grants-2012_03
Patent number
US08138179B2

Reaction notes

Loading…