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

HRID 480215Notes

Reaction equation

HRID 480215 reaction equation
[BH4-].[Na+].[C:3]([O:11][C@@H:12]1[CH2:20][C@@H:15]2[O:16][C:17](=[O:19])[CH2:18][C@@H:14]2[C@H:13]1[CH:21]=[O:22])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(Cl)Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:3]([O:11][C@@H:12]1[CH2:20][C@@H:15]2[O:16][C:17](=[O:19])[CH2:18][C@@H:14]2[C@@H:13]1[CH2:21][OH:22])(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 11000244(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Product 1

HCID 7156973(3aR,4R,5R,6aS)-4-(Hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoateYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of sodium borohydride (650 mg, 17.1 mmol) in methanol (20 mL) at 0° C. (bath temperature) was added a solution of (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one-4-carboxaldehyde (1) (3.5 g, 12.8 mmol) as a solution in 1:1 methanol:methylene chloride (40 mL). After 25 min, saturated citric acid was added cautiously (60 mL), the mixture was extracted with ethyl acetate (3×40 mL), the combined organic layers were washed with water (2×80 mL) and saturated brine (2×80 mL), dried (magnesium sulfate), filtered, and concentrated to afford 2 (2.43 g, 69%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×40 mL)
  2. washthe combined organic layers were washed with water (2×80 mL) and saturated brine (2×80 mL)
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a0c8e8aeeaa847d2962d48d217a40dd7
Source dataset
uspto-grants-2003_11
Patent number
US06649655B2

Reaction notes

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