N-(methoxycarbonyl)-4-keto-D-proline methyl ester → N-(methoxycarbonyl)-cis-4-hydroxy-D-proline methyl ester

HRID 583009

Reaction equation

HRID 583009 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C@H:4]1[CH2:8][C:7](=[O:9])[CH2:6][N:5]1[C:10]([O:12][CH3:13])=[O:11].[H][H]>C(OCC)(=O)C.[Pt]>[CH3:1][O:2][C:3](=[O:14])[C@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][CH3:13])=[O:11].[CH3:1][O:2][C:3](=[O:14])[C@H:4]1[CH2:8][C@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 2

HCID 11275680N-(methoxycarbonyl)-4-keto-D-proline methyl esterHCID 178418361HCID 178418361, compound

Product 2

HCID 21310449N-(methoxycarbonyl)-cis-4-hydroxy-D-proline methyl esterHCID 21310450N-(methoxycarbonyl)-trans-4-hydroxy-D-proline methyl ester

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 5.0 mL solution of 0.125 g of N-(methoxycarbonyl)-4-keto-D-proline methyl ester in ethyl acetate was mixed with 12.5 mg of 5% platinum on alumina under 70 psig of hydrogen at 25° C. After 18 h, the yields of N-(methoxycarbonyl)-cis-4-hydroxy-D-proline methyl ester and N-(methoxycarbonyl)-trans-4-hydroxy-D-proline methyl ester were 98.7% and 1.3%, respectively, with no N-(methoxycarbonyl)-4-keto-D-proline methyl ester remaining.

Sources & evidence

ORD record
ord-b27de7f916044eaf81ca0ee908401ded
Source dataset
uspto-grants-1999_07
Patent number
US05928933

Linked notes

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