HCID 22842581, compound → HCID 54147113, compound

HRID 2371412Notes

Reaction equation

HRID 2371412 reaction equation
[N+](C1C=CC(COC([N:12]2[CH2:16][C@H:15]([OH:17])[CH2:14][C@H:13]2[CH2:18][CH2:19][C:20]([NH:22][CH3:23])=[O:21])=O)=CC=1)([O-])=O.[H][H]>O1CCCC1.C(O)C.[C].[Pd]>[CH3:23][NH:22][C:20]([CH2:19][CH2:18][C@@H:13]1[CH2:14][C@@H:15]([OH:17])[CH2:16][NH:12]1)=[O:21]

Participants

6

Reactant 2

HCID 22842581HCID 22842581, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54147113HCID 54147113, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,4R)-1-p-nitrobenzyloxycarbonyl-2-(2-methylaminocarbonylethyl)-4-hydroxypyrrolidine (1.52 g) in tetrahydrofuran (15 ml) and ethanol (15 ml), 10 palladium-carbon (228 mg) was added. The mixture was stirred at room temperature for 3.5 hours under an atmospheric pressure of hydrogen. The reaction mixture was filtered to remove the catalyst. The filtrate was concentrated, and the residue was combined with water, washed with dichloromethane and lyophilized to give (2R,4R)-2-(2-methylaminocarbonylethyl)-4-hydroxypyrrolidine.

Workup

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

Sources & evidence

ORD record
ord-aea0a3eb879a4d34a795ccad280a9e80
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

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