tert-Butylsulfinamide, (R)-(+)- → HCID 87332461, compound

HRID 1039700Notes

Reaction equation

HRID 1039700 reaction equation
[F:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:3]=O.[CH3:11][C:12]([S@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>[Cu](Cl)Cl.C(Cl)Cl>[F:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)/[CH:3]=[N:17]/[S@@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16]

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 12602096HCID 12602096, compound

Product 1

HCID 87332461HCID 87332461, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a 500 mL RBF containing 2-fluoro-2-phenylacetaldehyde (320.00 mg, 2316.5 μmol) was added DCM (10 mL) and the mixture was allowed to stir at 23° C. for 2 min. At this time, (R)-2-methylpropane-2-sulfinamide (364.99 mg, 3011.5 μmol) was added in one portion to the mixture followed by copper(II) chloride (856.51 mg, 6370.4 μmol) at 5:30 pm. The reaction was allowed to stir overnight and then filtered through a plug of celite over silica gel. The solvent was removed and the crude residue was purified on a silica gel column (15 to 35% EtOAc in hexanes) to give the product (168 mg, 30%).

Workup

  1. stirringto stir overnight
  2. filtrationfiltered through a plug of celite over silica gel
  3. customThe solvent was removed
  4. customthe crude residue was purified on a silica gel column (15 to 35% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4695ebd9adab4bc5ba5f851ea0a6775f
Source dataset
uspto-grants-2013_10
Patent number
US08552181B2

Reaction notes

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