Tetrahydrofuran → HCID 67296116, compound

HRID 2276845Notes

Reaction equation

HRID 2276845 reaction equation
O1CCCC1.[F:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17](=O)[CH3:18])=[CH:9][CH:8]=1.[C:20]([S@:24]([NH2:26])=[O:25])([CH3:23])([CH3:22])[CH3:21].[BH4-].[Na+]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].O.CO>[F:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C@H:17]([NH:26][S:24]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:25])[CH3:18])=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 675681-(4-Fluoro-1-naphthyl)ethan-1-oneHCID 4311764Sodium borohydrideHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 67296116HCID 67296116, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

Titanium tetraisopropoxide (3.0 mL, 10 mmol) was added to a tetrahydrofuran (20 mL) solution of 4′-fluoro-1′-acetonaphthone 0.94 mL (6.0 mmol) and (R)-(+)-tert-butyl sulfinamide (610 mg, 5.0 mmol), and the mixture was heated under reflux for one full day. The reaction mixture was cooled to −78° C., followed by addition of sodium borohydride (0.76 g, 20 mmol), and then the temperature of the mixture was gradually raised to room temperature. Methanol (5 mL) and then water (20 mL) were added to the mixture under ice-cooling conditions, and the solid matter generated was filtered. The oil obtained was extracted with methylene chloride (20 mL), the organic phase was dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography (ethyl acetate/hexane:67/33) to give the title compound (527 mg, 45%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one full day
  3. temperaturethe temperature of the mixture was gradually raised to room temperature
  4. temperaturecooling conditions
  5. filtrationthe solid matter generated was filtered
  6. customThe oil obtained
  7. extractionwas extracted with methylene chloride (20 mL)
  8. dry with materialthe organic phase was dried over sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe crude product was purified by silica gel column chromatography (ethyl acetate/hexane:67/33)

Sources & evidence

ORD record
ord-345c7894e7254cdc92702533d065fdd4
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

Loading…