4-Nitrobenzenesulfonyl chloride → tert-butyl (2R)-2-({[(4-nitrophenyl)sulfonyl]oxy}methyl)aziridine-1-carboxylate

HRID 498991Notes

Reaction equation

HRID 498991 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[CH2:12][N:11]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.[N+:43]([C:46]1[CH:51]=[CH:50][C:49]([S:52](Cl)(=[O:54])=[O:53])=[CH:48][CH:47]=1)([O-:45])=[O:44]>C1COCC1.CCOCC.CN(C1C=CN=CC=1)C.C(Cl)Cl>[N+:43]([C:46]1[CH:47]=[CH:48][C:49]([S:52]([O:8][CH2:9][C@H:10]2[CH2:12][N:11]2[C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])(=[O:54])=[O:53])=[CH:50][CH:51]=1)([O-:45])=[O:44]

Participants

8

Reactant 4

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 11033505tert-butyl (2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)aziridine-1-carboxylate

Product 1

HCID 53381222tert-butyl (2R)-2-({[(4-nitrophenyl)sulfonyl]oxy}methyl)aziridine-1-carboxylateYield 57%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 21868444Ether tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl (2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)aziridine-1-carboxylate (prepared following literature procedures: Travins, J. M.; Etzkorn, F. A. Tetrahedron Lett. 1998, 39, 9389-9392) in THF/Et2O (1/1) (0.17 M) was cooled in an ice bath and treated dropwise over 20 min with 1 M TBAF in THF (1.05 eq). The resulting solution was stirred in the ice bath for 30 min, before being quenched by the addition of sat. aq. NaHCO3 and extracted into Et2O/PE (4/1). The organic layers were collected, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was taken up in dry DCM (0.17 M) and TEA (1.3 eq) introduced prior to cooling to 0° C. DMAP (0.1 eq) and 4-nitrobenzenesulfonyl chloride (1.1 eq) were added and the resulting mixture left to stir at RT overnight. The reaction mixture was diluted with DCM and washed with sat. aq. NaHCO3, water and brine before drying over Na2SO4, filtering and concentrating in vacuo. The crude was purified by FC (PE/EtOAc 80:20) to afford the title compound as an off-white solid (57%). (ES+) m/z 359 (M+H)+

Workup

  1. custombefore being quenched by the addition of sat. aq. NaHCO3
  2. extractionextracted into Et2O/PE (4/1)
  3. customThe organic layers were collected
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. waitthe resulting mixture left
  9. washwashed with sat. aq. NaHCO3, water and brine
  10. dry with materialbefore drying over Na2SO4
  11. filtrationfiltering
  12. concentrationconcentrating in vacuo
  13. customThe crude was purified by FC (PE/EtOAc 80:20)

Sources & evidence

ORD record
ord-3d40232e68614fcd9a24af5f77c05c5f
Source dataset
uspto-grants-2010_08
Patent number
US07767660B2

Reaction notes

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