HCID 53836703, compound → HCID 54497640, compound

HRID 1068209Notes

Reaction equation

HRID 1068209 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CCOC(C)=O.CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 53836703HCID 53836703, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54497640HCID 54497640, compoundYield 96.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 74 mg (0.21 mmol) of 1-tert-butoxycarbonyl-4-((3-benzyl)phenyl)-1,2,3,6-tetrahydropyridine (from Step D) and 6 mg of 10% palladium on carbon in 1 mL of EtOAc and 3 mL of MeOH was hydrogenated at 40 psi of hydrogen on a Parr shaker for 3 hours. The reaction was filtered and concentrated under reduced pressure to yield 71 mg (95%) of the title compound, which was used without further purification. 1H NMR (500 MHz, CDCl3) δ1.43-1.83 (m, 13H), 2.62 (m, 1H), 2.80 (m, 2H), 3.99 (s, 2H), 4.25 (m, 2H), 7.06-7.33 (m, 9H).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-82e853b8f84e4a5199212ca4dfe6d76b
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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