Hydrochloric Acid → HCID 53793002, compound

HRID 1741620Notes

Reaction equation

HRID 1741620 reaction equation
[CH:1]([C:4]1([CH3:23])[C:8](=[O:9])[NH:7][C:6]([C:10]2[N:19]=[CH:18][C:17]([CH:20]=[CH:21][CH3:22])=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[N:5]1)([CH3:3])[CH3:2].Cl.C([BH3-])#N.[Na+]>CO>[CH:1]([C:4]1([CH3:23])[C:8](=[O:9])[NH:7][CH:6]([C:10]2[N:19]=[CH:18][C:17]([CH:20]=[CH:21][CH3:22])=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])[NH:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 5003444Sodium cyanoborohydrideHCID 54120843HCID 54120843, compound

Product 1

HCID 53793002HCID 53793002, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.0 g of methyl 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2 -yl)-5-propenylnicotinate in 50 mL of absolute methanol is cooled in an ice bath to 2° and the pH is adjusted to 3 with dilute methanolic hydrogen chloride. Sodium cyanoborohydride is added in small portions, with maintenance of the pH at 3 by concurrent addition of dilute methanolic hydrogen chloride, until the disappearance of the starting material is indicated by TLC. The reaction mixture is concentrated in vacuo, and the residue is chromatographed on silica gel using hexane-ethyl acetate mixtures as eluant to give the cis and trans products as solids.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe residue is chromatographed on silica gel
  3. customto give the cis and trans products as solids

Sources & evidence

ORD record
ord-ee23161a185849129770da3812046250
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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