HCID 89962592, compound → HCID 89963559, compound

HRID 337988Notes

Reaction equation

HRID 337988 reaction equation
[C:1]([O:9][C@H:10]1[CH2:15][C@H:14]([O:16]CC2C=CC=CC=2)[CH2:13][CH2:12][C@@H:11]1[C:24]1[N:28]([CH2:29][O:30][CH2:31][CH2:32][O:33][CH3:34])[N:27]=[CH:26][CH:25]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[C@@H]1CC[C@H](OCC2C=CC=CC=2)C[C@@H]1C1N(COCCOC)N=CC=1)(=O)C1C=CC=CC=1>C(O)C.[C].[Pd]>[C:1]([O:9][C@H:10]1[CH2:15][C@H:14]([OH:16])[CH2:13][CH2:12][C@@H:11]1[C:24]1[N:28]([CH2:29][O:30][CH2:31][CH2:32][O:33][CH3:34])[N:27]=[CH:26][CH:25]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 89962592HCID 89962592, compoundHCID 89963316HCID 89963316, compound

Product 1

HCID 89963559HCID 89963559, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of the mixture (2.72 g, 5.84 mmol) of (1S*,2R*,5R*)-5-(benzyloxy)-2-{1-[(2-methoxyethoxy)methyl]-1H-pyrazol-5-yl}cyclohexyl benzoate and (1R*,2R*,4S*)-4-(benzyloxy)-2-{1-[(2-methoxyethoxy)methyl]-1H-pyrazol-5-yl}cyclohexyl benzoate prepared in Example 155c and palladium carbon (5%; 3.00 g) in ethanol (20 mL) was stirred at 50° C. for 11 hours under a hydrogen atmosphere. The reaction solution was filtered through celite, the filtrate was concentrated, and the residue was purified with silica gel chromatography (ethyl acetate) to yield the title compound (1.06 g, 48%) as a colorless oil.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified with silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-9288335cdf704e04a96245b38aed596c
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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