HCID 68678151, compound → HCID 58728069, compound

HRID 1992206Notes

Reaction equation

HRID 1992206 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:26][CH2:27][N:28]3[C@H:33]4[CH2:34][CH2:35][C@@H:29]3[CH2:30][CH:31]([N:36]3[C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=5[N:38]=[C:37]3[CH3:45])[CH2:32]4)[CH2:13][CH2:12][N:11]([CH:14]([CH3:25])[C:15]([O:17]CC3C=CC=CC=3)=[O:16])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:26][CH2:27][N:28]3[C@H:33]4[CH2:34][CH2:35][C@@H:29]3[CH2:30][CH:31]([N:36]3[C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=5[N:38]=[C:37]3[CH3:45])[CH2:32]4)[CH2:13][CH2:12][N:11]([CH:14]([CH3:25])[C:15]([OH:17])=[O:16])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 68678151HCID 68678151, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58728069HCID 58728069, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl 2-(4-(3-fluorophenyl)-4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}piperidin-1-yl)propanoate (136 mg, 0.223 mmol) in 8 mL MeOH was stirred for 3 h under an atmospheric pressure of hydrogen and in the presence of catalytic 5% Pd/C. Filtration and evaporation afforded 2-(4-(3-fluorophenyl)-4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}piperidin-1-yl)propanoic acid (90.0 mg, 78%) as a solid. 1H NMR (400 MHz, CDCl3), δ 7.69 (m, 1H), 7.40 (m, 1H), 7.26-7.12 (m, 4H), 7.09-6.95 (m, 2H), 5.37 (m, 1H), 3.85-3.55 (m, 5H), 2.81-1.77 (18H), 2.62 (s, 3H), 1.61-1.41 (3H); ESI-MS 517 (M−H).

Workup

  1. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-283804ba30654010b83c726f2cb124e0
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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