(2S,4R,5R)-4-Isopropenyl-5-[4-methoxy-3-(3-methoxy-propoxy)-phenyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester → (2S,4S,5R)-4-Isopropyl-5-[4-methoxy-3-(3-methoxy-propoxy)-phenyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

HRID 1009831Notes

Reaction equation

HRID 1009831 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C@@H:6]1[CH2:10][C@H:9]([C:11]([CH3:13])=[CH2:12])[C@H:8]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[CH:15]=2)[N:7]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:5]>C1(C)C=CC=CC=1.[Pd]>[CH3:1][CH2:2][O:3][C:4]([C@@H:6]1[CH2:10][C@@H:9]([CH:11]([CH3:13])[CH3:12])[C@H:8]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[CH:15]=2)[N:7]1[C:28]([O:30][C:31]([CH3:34])([CH3:32])[CH3:33])=[O:29])=[O:5]

Participants

4

Reactant 1

HCID 16124546(2S,4R,5R)-4-Isopropenyl-5-[4-methoxy-3-(3-methoxy-propoxy)-phenyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Product 1

HCID 16124547(2S,4S,5R)-4-Isopropyl-5-[4-methoxy-3-(3-methoxy-propoxy)-phenyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of (2S,4R,5R)-4-Isopropenyl-5-[4-methoxy-3-(3-methoxy-propoxy)-phenyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester VIIa (0.3 g) in 10 mL of toluene is treated with 50 mg of 5% palladium on carbon. The suspension is stirred under an atmosphere of hydrogen for 2 hours at room temperature and filtered. The solvent is removed in vacuum to give the desired compound as an oil.

Workup

  1. filtrationfiltered
  2. customThe solvent is removed in vacuum

Sources & evidence

ORD record
ord-18f6c428766c43a7be78b60541df00d2
Source dataset
uspto-grants-2011_07
Patent number
US07973175B2

Reaction notes

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