diisopropyl (2S,3R)-2-hydroxy-3-{(2E)-3-[4-(trifluoromethoxy)phenyl]-2-propenyl}butanedioate → diisopropyl (2S,3R)-2-hydroxy-3-{3-[4-(trifluoromethoxy)phenyl]propyl}butanedioate

HRID 1677790Notes

Reaction equation

HRID 1677790 reaction equation
[OH:1][C@@H:2]([C@@H:9]([CH2:16]/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=1)[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])[C:3]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4].[H][H]>CO.[Pd]>[OH:1][C@@H:2]([C@@H:9]([CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]([F:27])([F:28])[F:29])=[CH:21][CH:20]=1)[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])[C:3]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4]

Participants

5

Reactant 2

HCID 58488014diisopropyl (2S,3R)-2-hydroxy-3-{(2E)-3-[4-(trifluoromethoxy)phenyl]-2-propenyl}butanedioateHCID 178418361HCID 178418361, compound

Product 1

HCID 58487998diisopropyl (2S,3R)-2-hydroxy-3-{3-[4-(trifluoromethoxy)phenyl]propyl}butanedioateYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of diisopropyl (2S,3R)-2-hydroxy-3-{(2E)-3-[4-(trifluoromethoxy)phenyl]-2-propenyl}butanedioate (6.98 g; 16.68 mmol; 1.00 eq.) in methanol (105 mL) under N2 atmosphere was added Pd—C (10%; 200 mg; 0.17 mmol; 0.01 eq.). The mixture was then hydrogenated under 2 bars of hydrogen for 14 h at RT. The reaction mixture was then filtered and evaporated to obtain the title compound (6.95 g; 99.1%).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customevaporated

Sources & evidence

ORD record
ord-9e2296a9744b455b81e39222b3010a0d
Source dataset
uspto-grants-2011_08
Patent number
US08008302B2

Reaction notes

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