Sodium borohydride → HCID 67490895, compound

HRID 1917417Notes

Reaction equation

HRID 1917417 reaction equation
O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+].[C:14]([O:18][C:19]([C@H:21]1[C@H:25]([C:26]([CH:28]=[O:29])=[CH2:27])[CH2:24][N:23]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>C(O)C>[C:14]([O:18][C:19]([C@H:21]1[C@H:25]([C:26]([CH2:28][OH:29])=[CH2:27])[CH2:24][N:23]([C:30]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 86664656HCID 86664656, compound

Product 1

HCID 67490895HCID 67490895, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Cerium (III) chloride heptahydrate (57.0 g, 153 mmol) was dissolved in ethanol (700 mL). Sodium borohydride (5.79 g, 153 mmol) was added at 0° C., and the mixture was stirred for 10 minutes. A solution of (3S,4R)-1-benzyloxycarbonyl-4-(1-formylvinyl)pyrrolidine-3-carboxylic acid tert-butyl ester (55.0 g, 153 mmol) in ethanol (700 mL) was added dropwise to the reaction solution at 0° C., and the mixture was stirred at room temperature for three hours. The reaction solution was extracted with a 10% citric acid solution, water, and ethyl acetate. Then, the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=24:1→2:1) to give 42.2 g of the title compound as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for three hours
  2. extractionThe reaction solution was extracted with a 10% citric acid solution, water, and ethyl acetate
  3. washThen, the organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=24:1→2:1)

Sources & evidence

ORD record
ord-e5dde817f5524bd9bb5df883f36e20c8
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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