Hydrochloric Acid → (3S)-3-hydroxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

HRID 891726Notes

Reaction equation

HRID 891726 reaction equation
C([O:4][C@H:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[CH2:6]1)(=O)C.C[O-].[Na+].Cl>CO.O1CCOCC1>[OH:4][C@H:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 69544124(3S)-3-acetoxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 69544006(3S)-3-hydroxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidineYield 84.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (3S)-3-acetoxy-1-(p-nitrobenzyloxycarbonyl)-pyrrolidine (5.51 g, 17.8 mmol) (obtained as described in Reference Example 53(1)) in methanol (200 ml) was added a catalytic amount of sodium methoxide, and the mixture was stirred at room temperature for 4.5 hours. After checking the completion of the reaction, a solution of 4N hydrogen chloride in 1,4-dioxane (4.3 ml) was added thereto to neutralize the reaction mixture. The resulting reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with 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 (1:2)→ethyl acetate as the eluant to afford (3S)-3-hydroxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine (4.00 g, yield 84%) as white crystals.

Workup

  1. customthe completion of the reaction
  2. customThe resulting reaction mixture
  3. customwas partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution, dried 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-50591fb9807d4dda8ed2de72e8c0cc48
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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