Cerium(III) chloride → HCID 68460771, compound

HRID 503025Notes

Reaction equation

HRID 503025 reaction equation
[BH4-].[Na+].[Cl-].[Ce+3].[Cl-].[Cl-].[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]=[CH:26]/[C:27](=[O:34])[CH:28]([CH3:33])[CH2:29][CH2:30][CH2:31][CH3:32])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl-].[NH4+]>C(Cl)Cl.CO.C(OCC)(=O)C.O>[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]=[CH:26]/[C@@H:27]([OH:34])[CH:28]([CH3:33])[CH2:29][CH2:30][CH2:31][CH3:32])(=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

9

Reactant 4

HCID 24636Cerium(III) chlorideHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 68459257HCID 68459257, compound

Product 1

HCID 68460771HCID 68460771, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A slurry of sodium borohydride (1.8 g, 48 mmol) and cerium chloride (9 g, 24 mmol) in a mixture of methylene chloride (300 mL) and methanol (600 mL) was stirred at room temperature as a solution of (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-[(1E)-4-methyl-3-oxo-1-octenyl]-2H-cyclopenta[b]furan-2-one (9.3 g, 24 mmol) in 100 mL of methylene chloride was added. After 30 min, the reaction was treated with water, a saturated ammonium chloride solution, and ethyl acetate. The combined organic layers were dried and concentrated. Purification by normal phase chromatography using a gradient of ethyl acetate in hexane gave (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-[(1E,3S)-3-hydroxy-4-methyl-1-octenyl]-2H-cyclopenta[b]furan-2-one and 3.2 g of the second eluted compound which is the corresponding 3R-isomer, (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-[(1E,3R)-3-hydroxy-4-methyl-1-octenyl]-2H-cyclopenta[b]furan-2-one.

Workup

  1. additionwas added
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customPurification by normal phase chromatography

Sources & evidence

ORD record
ord-21d17487e6b240b5af11780dd236bc6b
Source dataset
uspto-grants-2010_08
Patent number
US07776896B2

Reaction notes

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