p-{3-[2-(1-Hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinylmethyl}cinnamic Acid → p-{3-[2-(1-Hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinylmethyl}hydrocinnamic Acid

HRID 443672Notes

Reaction equation

HRID 443672 reaction equation
[OH:1][C:2]1([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[CH2:13][S:12][CH:11]2[CH2:16][C:17]2[CH:27]=[CH:26][C:20]([CH:21]=[CH:22][C:23]([OH:25])=[O:24])=[CH:19][CH:18]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[H][H]>C(O)C.[Pd]>[OH:1][C:2]1([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[CH2:13][S:12][CH:11]2[CH2:16][C:17]2[CH:27]=[CH:26][C:20]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:19][CH:18]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 53980169p-{3-[2-(1-Hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinylmethyl}cinnamic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 23468090p-{3-[2-(1-Hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinylmethyl}hydrocinnamic Acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

p-{3-[2-(1-Hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinylmethyl}cinnamic Acid (7.8 g., 0.02 mole) in ethanol (125 ml.) is hydrogenated over 2.5 g. of a 5% Pd on charcoal catalyst at 1 atmosphere pressure and 27° C. When the theoretical amount (0.02 mole) of hydrogen has been absorbed, the catalyst is filtered off, the solvent evaporated, and the residue chromatographed on silica gel with 4% methanol in chloroform as the eluant. The title compound is obtained as a colorless, viscous oil.

Workup

  1. customat 1 atmosphere pressure and 27° C
  2. filtrationthe catalyst is filtered off
  3. customthe solvent evaporated
  4. customthe residue chromatographed on silica gel with 4% methanol in chloroform as the eluant

Sources & evidence

ORD record
ord-32aae5cb8498426daaa11357b945a5ca
Source dataset
uspto-grants-1981_04
Patent number
US04260771

Reaction notes

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