Potassium Acetate → (3S)-3-acetoxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

HRID 891725Notes

Reaction equation

HRID 891725 reaction equation
CS([O:5][C@@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[CH2:7]1)(=O)=O.[C:24]([O-])(=[O:26])[CH3:25].[K+]>CN(C)C=O>[C:24]([O:5][C@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[CH2:7]1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 86590872HCID 86590872, compound

Product 1

HCID 69544124(3S)-3-acetoxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidineYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (3R)-3-methanesulfonyloxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine (7.50 g, 21.8 mmol) (obtained as described in Reference Example 52(2)) in dimethylformamide (225 ml) was added potassium acetate (6.41 g, 65.3 mmol), and the mixture was stirred in an oil bath (80° C.) overnight. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed successively with 10% aqueous sodium chloride solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (2:1→1:2) as the eluant to afford (3S)-3-acetoxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine (5.51 g, yield 82%) as white crystals.

Workup

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe organic layer was washed successively with 10% aqueous sodium chloride solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-6b48b65dc6cd428d91903a33c8752df8
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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