HCID 73603516, compound → HCID 73603519, compound

HRID 1774594Notes

Reaction equation

HRID 1774594 reaction equation
[C:1]([O:5][CH:6]([C:10]1[N:14]([CH3:15])[N:13]=[C:12]([C:16]2[CH2:20][CH2:19][CH2:18][CH:17]=2)[C:11]=1[C:21]1[CH:22]=[CH:23][C:24]2[O:29][CH2:28][CH2:27][CH2:26][C:25]=2[CH:30]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][CH:6]([C:10]1[N:14]([CH3:15])[N:13]=[C:12]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:11]=1[C:21]1[CH:22]=[CH:23][C:24]2[O:29][CH2:28][CH2:27][CH2:26][C:25]=2[CH:30]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 73603516HCID 73603516, compound

Product 1

HCID 73603519HCID 73603519, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(tert-butoxy)-2-[3-(cyclopent-1-en-1-yl)-4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-1H-pyrazol-5-yl]acetic acid (example 12) (19.7 mg, 0.047 mmol) and palladium on carbon (7 mg) in methanol (2.4 mL) was stirred under hydrogen atmosphere overnight. The mixture was filtered over Millipore and the filtrate was concentrated in vacuo to provide 2-(tert-butoxy)-2-[3-cyclopentyl-4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-1H-pyrazol-5-yl]acetic acid (example 19) (19.5 mg, 0.047 mmol, 98%) as a white solid.

Workup

  1. filtrationThe mixture was filtered over Millipore
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3075b3ede6aa4eb2ba29975aa3624197
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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