Sodium cyanoborohydride → HCID 19065570, compound

HRID 482150Notes

Reaction equation

HRID 482150 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:8]=[C:9]([C:13]3[CH2:17][CH2:16][C:15](=[N:18][OH:19])[CH:14]=3)[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[C:9]([C:13]3[CH2:17][CH2:16][CH:15]([NH:18][OH:19])[CH:14]=3)[CH:10]=[CH:11][CH:12]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydride2×HCID 73516783HCID 73516783, compound

Product 1

HCID 19065570HCID 19065570, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution of 3-[3-(4-fluorophenoxy)phenyl]-2-cyclopentenone oxime (1.85 g; 6.54 mM) in acetic acid (10 ml) was added sodium cyanoborohydride (0.62 g; 9.81 mM) portionwise at room temperature. After stirring for 2 hrs, additional sodium cyanoborohydride (0.25 g; 4 mM) and acetic acid (5 ml) was added. The mixture was stirred overnight. Acetic acid was removed in vacuo, and to the residue was added saturated aqueous NaHCO3 (50 ml). The whole was extracted with ethyl acetate (50 ml×1, 30 ml×1), and the combined organic layers were washed with water (50 ml), brine (50 ml), dried over MgSO4, and concentrated in vacuo. The residual oil was purified by flash column (SiO2) eluting with CH2Cl2 -ethanol (30:1) to give 1.07 g of the subtitle compound [F] as a pale yellow oil.

Workup

  1. stirringThe mixture was stirred overnight
  2. customAcetic acid was removed in vacuo
  3. additionto the residue was added saturated aqueous NaHCO3 (50 ml)
  4. extractionThe whole was extracted with ethyl acetate (50 ml×1, 30 ml×1)
  5. washthe combined organic layers were washed with water (50 ml), brine (50 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residual oil was purified by flash column (SiO2)
  9. washeluting with CH2Cl2 -ethanol (30:1)

Sources & evidence

ORD record
ord-4924d31f898f4f84bfe17a1e2fcc338d
Source dataset
uspto-grants-1998_08
Patent number
US05792882

Reaction notes

Loading…