tert-Butylsulfinamide, (R)-(+)- → HCID 178465718, compound

HRID 1053684Notes

Reaction equation

HRID 1053684 reaction equation
[CH3:1][C:2]([S@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[Br:8][C:9]1[C:10]([CH3:18])=[C:11]([C:15](=O)[CH3:16])[CH:12]=[CH:13][CH:14]=1>C1COCC1.C(O[Ti](OCC)(OCC)OCC)C>[Br:8][C:9]1[C:10]([CH3:18])=[C:11](/[C:15](=[N:7]/[S@@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])/[CH3:16])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 204801311-(3-Bromo-2-methylphenyl)ethanone

Product 1

HCID 178465718HCID 178465718, compound

Reagents, catalysts & solvents 2

HCID 178477244HCID 178477244, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a stirring solution of (R)-2-methylpropane-2-sulfinamide (326 mg, 2.69 mmol) and Intermediate 12A (600 mg, 2.82 mmol) in THF (2 mL) at rt was added tetraethoxytitanium (1.06 mL, 5.12 mmol). The reaction mixture was heated at 75° C. for 16 h. The reaction mixture was cooled and used directly in the next step. LCMS=2.12 min [M+1]=318.0 (Method B).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customLCMS=2.12 min [M+1]=318.0 (Method B)

Sources & evidence

ORD record
ord-d892c17472244c0eb000762b3c79055c
Source dataset
uspto-grants-2016_07
Patent number
US09394260B2

Reaction notes

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