HCID 57907463, compound → HCID 57907386, compound

HRID 1888153Notes

Reaction equation

HRID 1888153 reaction equation
[N:1]1[N:2]2[CH:8]([C:9]([O:11]CC3C=CC=CC=3)=[O:10])[CH2:7][CH2:6][C:3]2=[CH:4][CH:5]=1.[H][H]>[Pd].C(O)C>[N:1]1[N:2]2[CH:8]([C:9]([OH:11])=[O:10])[CH2:7][CH2:6][C:3]2=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 57907463HCID 57907463, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57907386HCID 57907386, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A 100 mL round bottom flask under an atmosphere of nitrogen was charged with 0.600 mg (0.560 mmol) of 10 weight percent palladium on activated carbon and wet with 10 ml of ethanol. Next, a solution of 6.0 g (0.025 mol) of benzyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-6-carboxylate from step F in 40 mL of ethanol was added and the mixture placed under 1 atmosphere of hydrogen. The reaction was stirred for 3 h then filtered through a pad of Celite®. The pad was washed with 20 mL of ethanol and the filtrate was evaporated in vacuo to afford the title compound as a colorless solid (3.7 g, quantitative yield). 1H NMR (500 MHz, DMSO-d6): δ 11.90 (br s, 1H), 7.44 (s, 1H), 5.98 (s, 1H), 4.87 (dd, J=8.9, 3.7 Hz, 1H), 2.94-2.82 (m, 3H), 2.58-2.52 (m, 1H). LC-MS: m/z (ES) 153 (MH)+.

Workup

  1. filtrationthen filtered through a pad of Celite®
  2. washThe pad was washed with 20 mL of ethanol
  3. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-a8929bb8c0a142e68a12c837458331ad
Source dataset
uspto-grants-2013_08
Patent number
US08501786B2

Reaction notes

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