Toluene → HCID 86705520, compound

HRID 2279521Notes

Reaction equation

HRID 2279521 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[O:4][CH2:3][C@@H:2]1/[CH:11]=[N:12]\[S@:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14].C1(C)C=CC=CC=1.[Cl:26][C:27]1[CH:28]=[C:29]([Mg]Br)[CH:30]=[CH:31][C:32]=1[Cl:33]>O>[Cl:26][C:27]1[CH:28]=[C:29]([C@@H:11]([C@H:2]2[CH2:3][O:4][C:5]3([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]3)[O:1]2)[NH:12][S@:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])[CH:30]=[CH:31][C:32]=1[Cl:33]

Participants

5

Reactant 3

HCID 1140TolueneHCID 141625679HCID 141625679, compoundHCID 178478192HCID 178478192, compound

Product 1

HCID 86705520HCID 86705520, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 248 (2.0 g, 7.3 mmol) and toluene (30 mL) cooled to −78° C. was added (3,4-dichlorophenyl)magnesium bromide (29 mL, 15 mmol) and warmed to 0° C. for 30 min. The reaction was poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (4:1 to 1:1) to afford 1.8 g (59%) of (S)—N—((S)-(3,4-dichlorophenyl)((S)-1,4-dioxaspiro[4.5]decan-2-yl)methyl)-2-methylpropane-2-sulfinamide (250) which appears to be a ca. 10:1 mixture of diastereomers by 1H NMR.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with a hexane/EtOAc gradient (4:1 to 1:1)

Sources & evidence

ORD record
ord-d1b2e47ab0fd44f2b9d778e290c180d0
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

Loading…