Keto-pantoyllactone → (+-)-Pantolactone

HRID 1357345Notes

Reaction equation

HRID 1357345 reaction equation
[O:1]=[C:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][O:5][C:3]1=[O:4].[H][H]>C1COCC1>[OH:1][CH:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][O:5][C:3]1=[O:4]

Participants

4

Reactant 2

HCID 39Keto-pantoyllactoneHCID 178418361HCID 178418361, compound

Product 1

HCID 989(+-)-Pantolactone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Oxo-3,3-dimethyl-γ-butyrolactone (18) was hydrogenated according to General Procedure B in THF at 20.7 barg (300 psig) hydrogen at ambient temperature using bis(1,5-cyclooctadiene)rhodium trifluoromethanesulfonate (2.3 mg; 5 μmol; 0.01 equiv) and ligand (S,R)-2g (3.7 mg; 6 μmol; 0.012 equiv) for 6 hours to afford 99.6% conversion to 2-hydroxy-3,3-dimethyl-γ-butyrolactone (19) with 97.2% ee as determined by chiral GC analysis.

Workup

  1. customfor 6 hours

Sources & evidence

ORD record
ord-308df87afbe0408eb592b3fb3c3ae21d
Source dataset
uspto-grants-2003_07
Patent number
US06590115B2

Reaction notes

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