HCID 89963068, compound → HCID 89963019, compound

HRID 338026Notes

Reaction equation

HRID 338026 reaction equation
[CH3:1][N:2]1[C:6]([C@@:7]23[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:8]2[O:9]C(=O)O3)=[CH:5][CH:4]=[N:3]1>C1COCC1.[C].[Pd]>[CH3:1][N:2]1[C:6]([C@@H:7]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:8]2[OH:9])=[CH:5][CH:4]=[N:3]1

Participants

4

Reactant 1

HCID 89963068HCID 89963068, compound

Product 1

HCID 89963019HCID 89963019, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the (3aS,7aS)-3a-(1-methyl-1H-pyrazol-5-yl)hexahydro-1,3-benzodioxol-2-one (500 mg, 2.25 mmol) prepared in Example 167a and palladium carbon (10%; 500 mg) in THF (10 mL) was stirred at 60° C. for 12 hours under a hydrogen atmosphere. The reaction solution was filtered through celite, and the residue was purified with silica gel chromatography (hexane/ethyl acetate=2:1) to yield the title compound (85 mg, 21%) as a colorless oil.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-96f09827c8dc44d0921a9622b63a4481
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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