2,3-Dimethyl-1-butene → 2-Isopropyl-2-methyl-1-tosylaziridine

HRID 251518

Reaction equation

HRID 251518 reaction equation
[CH3:1][C:2]([CH:4]([CH3:6])[CH3:5])=[CH2:3].[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([NH:17]Cl)(=[O:16])=[O:15])=[CH:12][CH:13]=1.[Br-].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C(#N)C>[CH:2]([C:4]1([CH3:6])[CH2:5][N:17]1[S:14]([C:11]1[CH:12]=[CH:13][C:8]([CH3:7])=[CH:9][CH:10]=1)(=[O:15])=[O:16])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 112492,3-Dimethyl-1-buteneHCID 31388TosylchloramideHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 468396432-Isopropyl-2-methyl-1-tosylaziridineYield 51.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2,3-dimethyl butene (300 ml, 2.42 mol) in 7.8 L of dry acetonitrile was added Chloramine-T (749.9 g, 1.1 eq) portionwise over 90 min. The temperature was maintained at approximately 20° C. To this reaction mixture was added phenyltrimethylammonium tribromide (91.4 g, 0.1 eq) in 10 g portions over 90 min. The temperature increased to 26° C. during the addition. The reaction mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated down to approximately 15% of the initial volume and was them filtered, washing the solid with 1 L of acetonitrile. The organic liquid phase was concentrated and the residue dissolved in 2.5 L of EtOAc. The resulting solution was washed twice with water, dried over MgSO4, and concentrated to give a solid. The crude was purified on a large plug of celite using gradient elution 5% to 25% EtOAc/heptanes to afford 317 g of 2-isopropyl-2-methyl-1-[(4-methylphenyl)sulfonyl]aziridine as a solid.

Workup

  1. temperatureThe temperature increased to 26° C. during the addition
  2. concentrationThe reaction mixture was concentrated down to approximately 15% of the initial volume
  3. filtrationfiltered
  4. washwashing the solid with 1 L of acetonitrile
  5. concentrationThe organic liquid phase was concentrated
  6. dissolutionthe residue dissolved in 2.5 L of EtOAc
  7. washThe resulting solution was washed twice with water
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customto give a solid
  11. customThe crude was purified on a large plug of celite
  12. washelution 5% to 25% EtOAc/heptanes

Sources & evidence

ORD record
ord-a023e41cb5164a91a85d4fe5bcaa25a7
Source dataset
uspto-grants-2011_01
Patent number
US07863465B2

Linked notes

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