Imidazole → (2R)-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1-[(4-fluoro-phenyl)sulfonyl]aziridine

HRID 475493Notes

Reaction equation

HRID 475493 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:13][C@H:12]2[CH2:14][CH2:15][OH:16])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19].N1C=CN=C1>C1COCC1>[Si:21]([O:16][CH2:15][CH2:14][C@@H:12]1[CH2:13][N:11]1[S:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9])([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 583991702-{(2R)-1-[(4-Fluorophenyl)sulfonyl]aziridin-2-yl}ethanol

Product 1

HCID 58399169(2R)-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1-[(4-fluoro-phenyl)sulfonyl]aziridineYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the 2-{(2R)-1-[(4-fluorophenyl)sulfonyl]aziridin-2-yl}ethanol from Step 3 dissolved in THF (0.2 M) was added TBSCl (1.1 equiv.) followed by imidazole (2.2 equiv.). The reaction mixture was stirred 1 h at rt, then filtered with washing of the solids with MTBE. The combined organics were washed (2×) with 1M HCl, brine (2×), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with EtOAc/Hex (1:9) to give the title compound (85%) as a white solid.

Workup

  1. filtrationfiltered
  2. washwith washing of the solids with MTBE
  3. washThe combined organics were washed (2×) with 1M HCl, brine (2×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluting with EtOAc/Hex (1:9)

Sources & evidence

ORD record
ord-6536ff5ee0764e0e88cde24222c7e017
Source dataset
uspto-grants-2014_01
Patent number
US08637541B2

Reaction notes

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