HCID 178472494, compound → HCID 178472495, compound

HRID 237326Notes

Reaction equation

HRID 237326 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][CH:13]([CH2:23][O:24]CC2C=CC=CC=2)[CH2:14][O:15]CC2C=CC=CC=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>C(O)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][CH:13]([CH2:23][OH:24])[CH2:14][OH:15])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 178472494HCID 178472494, compound

Product 1

HCID 178472495HCID 178472495, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To an argon purged solution of cis/trans-4-(2-benzyloxy-1-benzyloxymethyl-ethoxy)-cyclohexanecarboxylic acid ethyl ester (2.30 g, 5.39 mmol) in acetic acid (54 ml) was added palladium on charcoal 10% (0.57 g). The reaction mixture was purged with hydrogen gas and stirred at room temperature for 3 h under an atmosphere of hydrogen gas. The catalyst was removed by filtration over Decalite. The filtrate was concentrated in vacuo. Flash-chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.74 g, 56%) as colorless oil. MS m/e: 247 (M+H+)

Workup

  1. customThe reaction mixture was purged with hydrogen gas
  2. customThe catalyst was removed by filtration over Decalite
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-36298b323ede40348363ae99971aa6e2
Source dataset
uspto-grants-2014_02
Patent number
US08642590B2

Reaction notes

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