Trityl chloride → 1-(Triphenylmethyl)aziridine

HRID 1976204Notes

Reaction equation

HRID 1976204 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.[C:8](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CS(Cl)(=O)=O>C(Cl)Cl>[C:8]([N:3]1[CH2:6][CH2:7]1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride

Product 1

HCID 150816881-(Triphenylmethyl)aziridineYield 105.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Amine 182 (2.59 g, 10.2 mmol) was dissolved in 5% HCl/MeOH (30 mL) and the solution was stirred for 3 h at room temperature. Additional 5% HCl/MeOH (10 mL) was added stirring 1 h and the solvent was evaporated to afford 2.52 g of the HCl salt as a tan solid after high vacuum. To a suspension of the HC1 salt in CH2Cl2 (50 mL) at 0° C. was added triethylamine (3.55 mL, 25.5 mmol) followed by the addition of solid trityl chloride (5.55 g, 12.8 mmol) in one portion. The mixture was stirred at 0° C. for 1 h and then was warmed to room temperature stirring for 2 h. The reaction was cooled to 0° C., triethylamine (3.6 mL, 25.5 mmol) was added and methane sulfonyl chloride (0.97 mL, 12.5 mmol) was added, stirring the resulting mixture for 1 h at 0° C. and for 22 h at room temperature. The reaction was evaporated and the residue was partitioned between diethyl ether (200 mL) and water (200 mL). The organic phase was washed with water (200 mL) and the combined aqueous phases were extracted with diethyl ether (200 mL). The combined organic extracts were washed with water (100 mL), saturated NaCl (200 mL) and were dried (Na2SO4), filtered, and evaporated. The crude product was purified on silica gel (1/1-hexane/CH2Cl2) to afford N-trityl aziridine 183 (3.84 g, 86%) as a white foam: 1H NMR (CDCl3) δ 7.4-7.23 (m, 16H), 4.32 (m, 1H), 3.81 (s, 3H), 3.06 (dt, 1H, J=1.8, 17.1), 2.94-2.86 (m, 1H), 2.12 (m, 1H), 1.85 (t, 1H, J=5.0).

Workup

  1. temperaturewas warmed to room temperature
  2. stirringstirring for 2 h
  3. temperatureThe reaction was cooled to 0° C.
  4. stirringstirring the resulting mixture for 1 h at 0° C.
  5. waitfor 22 h at room temperature
  6. customThe reaction was evaporated
  7. customthe residue was partitioned between diethyl ether (200 mL) and water (200 mL)
  8. washThe organic phase was washed with water (200 mL)
  9. extractionthe combined aqueous phases were extracted with diethyl ether (200 mL)
  10. washThe combined organic extracts were washed with water (100 mL), saturated NaCl (200 mL)
  11. dry with materialwere dried (Na2SO4)
  12. filtrationfiltered
  13. customevaporated
  14. customThe crude product was purified on silica gel (1/1-hexane/CH2Cl2)

Sources & evidence

ORD record
ord-8f171531cd5144ba9d9e2782fcb28606
Source dataset
uspto-grants-2001_05
Patent number
US06225341B1

Reaction notes

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