Triacetoxyperiodinane → HCID 89370062, compound

HRID 712837Notes

Reaction equation

HRID 712837 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C@@H:4]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)=[O:19])[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[C:2]1[CH2:6][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:16])([F:17])[F:15])[CH:9]=2)[C@@H:4]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:29])[F:30])[CH:23]=2)=[O:19])[CH2:3]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86731617HCID 86731617, compound

Product 1

HCID 89370062HCID 89370062, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2R,4R)-3-(trifluoromethyl)benzyl 4-hydroxy-1-(3-(trifluoromethyl)benzyl)pyrrolidine-2-carboxylate (D81) (469 mg, 1.05 mmol) in dry DCM (10 ml) was treated with Dess-Martin periodinane (0.57 mg, 1.34 mmol) and stirred at RT 4 hrs. The reaction was quenched with 10% aqueous sodium sulphite solution (10 ml) and extracted with EtOAc (3×10 ml). The organic phases were collected, washed with NaCl sat. sol, dried over Na2SO4 and evaporated to afford a residue which was purified by SPE-Si cartridge (10 g) eluting with a mixture cHex/EtOAc 90/10. Collected fractions after solvent evaporation afforded the title compound (D83) (290 mg).

Workup

  1. customThe reaction was quenched with 10% aqueous sodium sulphite solution (10 ml)
  2. extractionextracted with EtOAc (3×10 ml)
  3. customThe organic phases were collected
  4. washwashed with NaCl sat. sol
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customto afford a residue which
  8. customwas purified by SPE-Si cartridge (10 g)
  9. washeluting with a mixture cHex/EtOAc 90/10
  10. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-86685b152e1b4de698d68c331de935f7
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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