Cornforth reagent → HCID 70976192, compound

HRID 455281Notes

Reaction equation

HRID 455281 reaction equation
[OH:1][C@@H:2]1[CH2:22][N:5]2[C:6](=[O:21])[N:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:11][CH:10]=3)[CH2:8][CH:4]2[CH2:3]1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[F:20][C:17]([F:18])([F:19])[CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([N:7]2[CH2:8][C@@H:4]3[CH2:3][C:2](=[O:1])[CH2:22][N:5]3[C:6]2=[O:21])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 70976286HCID 70976286, compound

Product 1

HCID 70976192HCID 70976192, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of (S)-6-Hydroxy-2-[4-(2,2,2-trifluoro-ethoxy)-phenyl]-hexahydro-pyrrolo[1,2-c]imidazol-3-one (1 g, 3.16 mmol) in dry DCM (20 mL) was added PDC (3.6 g, 9.48 mmol) portion wise under cooling. The reaction mixture was stirred at room temperature for 13 h. Then reaction mixture was filtered and washed with methanol, the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (elution with 30% ethyl acetate in hexane) to yield 500 mg (50%) of the title compound as white solid. LC-MS: 315.4 [M+1]+.

Workup

  1. temperatureunder cooling
  2. customThen reaction mixture
  3. filtrationwas filtered
  4. washwashed with methanol
  5. customthe filtrate was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (elution with 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-17d8f1bd4adf48b7ad3c421f5d6b1779
Source dataset
uspto-grants-2013_07
Patent number
US08497288B2

Reaction notes

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