Tetrahydrofuran → HCID 66686029, compound

HRID 1623086Notes

Reaction equation

HRID 1623086 reaction equation
[CH3:1][C:2]([CH3:16])([CH2:7][C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH3:6])=[O:4].[CH3:17][C:18]([S:21]([NH2:23])=[O:22])([CH3:20])[CH3:19].[BH4-].[Na+].[H][H].[CH2:28]1COCC1>[Cl-].[Na+].O.[O-]CC.[O-]CC.[O-]CC.[O-]CC.[Ti+4].CO>[C:18]([S:21]([NH:23][CH:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:7][C:2]([CH3:16])([CH3:1])[C:3]([O:5][CH2:6][CH3:28])=[O:4])=[O:22])([CH3:20])([CH3:19])[CH3:17]

Participants

9

Reactant 5

HCID 8028TetrahydrofuranHCID 3382465Tert-ButanesulfinamideHCID 4311764Sodium borohydrideHCID 18948507HCID 18948507, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66686029HCID 66686029, compound

Reagents, catalysts & solvents 3

HCID 76524Titanium tetraethoxideCatalystHCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of methyl 2,2-dimethyl-4-oxo-4-phenylbutanoate from Step A (0.51 g, 2.3 mmol) and 2-methylpropane-2-sulfinamide (0.34 g, 2.8 mmol) in THF (12 mL) was added titanium tetraethoxide (1.4 g, 5.6 mmol). This mixture was then heated to 60° C. for 3 days. After cooling to 0° C. in an ice bath, sodium borohydride (0.18 g, 4.7 mmol) was added. Following 90 minutes of stirring at 0° C., MeOH was added slowly (drop-wise) until hydrogen gas evolution ceased. Next, saturated brine (˜12 mL) was added, with vigorous stirring. The resulting mixture was filtered through celite using copious amounts of EtOAc. This organic filtrate was washed with saturated brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of EtOAc:Hexane—10:90 to 70:30, to give the title compound. MS: m/z=340 (M+1).

Workup

  1. temperatureAfter cooling to 0° C. in an ice bath
  2. filtrationThe resulting mixture was filtered through celite
  3. washThis organic filtrate was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of EtOAc

Sources & evidence

ORD record
ord-1a47d961cc794b82908ff3c32fb9dc3c
Source dataset
uspto-grants-2014_07
Patent number
US08778957B2

Reaction notes

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