2,4-Pyrrolidinedione → HCID 14427783, compound

HRID 346311Notes

Reaction equation

HRID 346311 reaction equation
[NH:1]1[CH2:5][C:4](=O)[CH2:3][C:2]1=O.[H][H].[CH3:10][OH:11].C([O:15][CH2:16][CH3:17])(=O)C>[Pt]=O>[CH:3]1([CH2:4][C@@H:5]2[NH:1][C:10](=[O:11])[CH2:17][C@@H:16]2[OH:15])[CH2:5][CH2:4][CH2:3][CH2:2][CH2:2]1

Participants

5

Reactant 3

HCID 5514912,4-PyrrolidinedioneHCID 21584119Ethylacetate methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 14427783HCID 14427783, compound

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

A solution of 20 g (0.102 mol) of (S)-5-cyclohexylmethyl)-2,4-pyrrolidinedione in 800 ml of 10% methanol-ethyl acetate is exposed to hydrogen gas in the presence of platinum oxide (this solution is charcoaled and filtered before reduction). After hydrogen uptake is complete, the catalyst is filtered and the filtrate concentrated under reduced pressure. The remaining white solid is triturated with 100 ml of diethyl ether, filtered and washed with diethyl ether to afford 19.3 g of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone after recrystallization from ethyl acetate; mp 141°-143° C.; [α]D23 =-19.9° (c=0.98% methanol).

Workup

  1. filtrationfiltered before reduction)
  2. filtrationthe catalyst is filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe remaining white solid is triturated with 100 ml of diethyl ether
  5. filtrationfiltered
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-44180e27380b4a9289d377539760be53
Source dataset
uspto-grants-1991_10
Patent number
US05061808

Reaction notes

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