HCID 71215527, compound → HCID 71215478, compound

HRID 271367Notes

Reaction equation

HRID 271367 reaction equation
C(OC(=O)[NH:10][C@H:11]1[CH2:15][CH2:14][C@H:13]([O:16][CH2:17][C:18]([F:27])([F:26])[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH2:12]1)C1C=CC=CC=1>[Pd].C(O)C>[F:26][C:18]([F:27])([C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=1)[CH2:17][O:16][C@H:13]1[CH2:14][CH2:15][C@H:11]([NH2:10])[CH2:12]1

Participants

4

Reactant 1

HCID 71215527HCID 71215527, compound

Product 1

HCID 71215478HCID 71215478, compoundYield 101.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 600 mg of trans [3-(2,2-Difluoro-2-p-tolyl-ethoxy)-cyclopentyl]-carbamic acid benzyl ester and 500 mg of 10% palladium on carbon in 25 mL of ethanol was stirred under an atmosphere of hydrogen for 2 h. Removal of the catalyst by filtration and concentration under reduced pressure gave 400 mg of product as an oil: MS (m+1)=256.3; 1H NMR (400 MHz, CDCl3) 7.4 (dd, 2H), 7.22 (dd, 2H), 4.05 (m, 1H), 3.75 (t, J=14 Hz, 2H), 3.5 (m, 1H), 2.4 (s, 3H), 2.2 (m, 2H), 2.0 (m, 2H), 1.62 (m, 1H), 1.5 (m, 1H), 1.24 (m, 1H).

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration and concentration under reduced pressure

Sources & evidence

ORD record
ord-4e4d1d96ed0041828bf6e6c41b666300
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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