Acetic Acid → HCID 67897488, compound

HRID 2371408Notes

Reaction equation

HRID 2371408 reaction equation
[N+](C1C=CC(COC([N:12]2[CH2:16][C@H:15]([OH:17])[CH2:14][C@H:13]2[CH2:18][O:19][C:20](=[O:22])[CH3:21])=O)=CC=1)([O-])=O.C(O)(=O)C.[H][H]>C(O)C.[C].[Pd]>[C:20]([OH:22])(=[O:19])[CH3:21].[C:20]([O:19][CH2:18][C@@H:13]1[CH2:14][C@@H:15]([OH:17])[CH2:16][NH:12]1)(=[O:22])[CH3:21]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 56629981HCID 56629981, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67897488HCID 67897488, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2S,4R)-1-p-nitrobenzyloxycarbonyl-2-acetoxymethyl-4-hydroxypyrrolidine (1.55 g) in ethanol (23 ml), 10% palladium-carbon (233 mg) and acetic acid (330 mg) were added. The mixture was stirred at room temperature for 2 hours under an atmospheric pressure of hydrogen. The reaction mixture was filtered to remove the catalyst. The filtrate was concentrated to remove the solvent. The residue was combined with water, washed with dichloromethane and concentrated to give (2S,4R)-2-acetoxymethyl-4-hydroxypyrrolidine acetate.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated
  4. customto remove the solvent
  5. washwashed with dichloromethane
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8196a9f9f6764514a4531620c28b48f6
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

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