Pyridine → (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

HRID 503024Notes

Reaction equation

HRID 503024 reaction equation
N1C=CC=CC=1.[C:7]([O:15][C@@H:16]1[CH2:24][C@@H:19]2[O:20][C:21](=[O:23])[CH2:22][C@@H:18]2[C@H:17]1[CH2:25][OH:26])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)Cl.C1(C)C=CC=CC=1.[O-2].[O-2].[O-2].[Cr+6]>[C:7]([O:15][C@@H:16]1[CH2:24][C@@H:19]2[O:20][C:21](=[O:23])[CH2:22][C@@H:18]2[C@H:17]1[CH:25]=[O:26])(=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 2

HCID 1049PyridineHCID 2724454(3aR,4S,5R,6aS)-5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one

Product 1

HCID 11000244(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of anhydrous chromium trioxide (20.8 g, 208 mmol) in methylene chloride (400 mL) was stirred and cooled in an ice bath as anhydrous pyridine (32.7 mL, 406 mmol) was added. After 15 min at 0° C., the mixture was allowed to warm to ambient temperature for 2 h. The reaction mixture was cooled to 0° C. and treated with a pre-cooled solution of (3aR,4S,5R,6aS)-5-(benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one (Corey lactone, 9.4 g, 34 mmol) in methylene chloride (400 mL) After 5 min, the reaction was diluted with toluene (240 mL) and filtered. The solid was washed with toluene. The combined filtrate was concentrated to give (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2-oxo-2H-cyclopenta[b]furan-4-carboxaldehyde. Toluene was added to give about 300 mL of solution.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. filtrationfiltered
  4. washThe solid was washed with toluene
  5. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-fe7250942d894c35af3f000855b3d029
Source dataset
uspto-grants-2010_08
Patent number
US07776896B2

Reaction notes

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