Sodium cyanoborohydride → HCID 22915412, compound

HRID 1377776Notes

Reaction equation

HRID 1377776 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH2:18][CH2:17][C:16](=[N:19][OH:20])[CH:15]=3)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[BH3-]C#N.[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH2:18][CH2:17][CH:16]([NH:19][OH:20])[CH:15]=3)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 74003791HCID 74003791, compound

Product 1

HCID 22915412HCID 22915412, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 3-[5-(4-fluorophenylthio)-2-furyl]-2-cyclopentenone oxime (6 g; 20.8 mM) in acetic acid (40 ml) was added NaBH3CN (1.57 g; 24.9 mM) at room temperature. After stirring for 2.5 hr, acetic acid was removed. The residue was dissolved in ethyl acetate (150 ml), and the whole was washed with saturated aqueous NaHCO3 (80 ml). The aqueous layer was extracted with ethyl acetate (80 ml), and the combined organic layer washed with water (80 ml), brine (80 ml), dried over MgSO4, and concentrated in vacuo. Chromatographic purification of the residue during with CH2Cl2 -EtOH (50: 1) provided 1.35 g (yield 22%) of the subtitle compound as a yellow oil.

Workup

  1. customacetic acid was removed
  2. dissolutionThe residue was dissolved in ethyl acetate (150 ml)
  3. washthe whole was washed with saturated aqueous NaHCO3 (80 ml)
  4. extractionThe aqueous layer was extracted with ethyl acetate (80 ml)
  5. washthe combined organic layer washed with water (80 ml), brine (80 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customChromatographic purification of the residue during with CH2Cl2 -EtOH (50: 1)

Sources & evidence

ORD record
ord-d924cd32a92c4720878183d1ace3724f
Source dataset
uspto-grants-1997_09
Patent number
US05665768

Reaction notes

Loading…