HCID 68678071, compound → HCID 68677588, compound

HRID 1992208Notes

Reaction equation

HRID 1992208 reaction equation
[CH:1]1([CH:7]([N:18]2[CH2:23][CH2:22][C:21]([C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([F:50])[CH:45]=3)([CH2:24][CH2:25][N:26]3[C@H:31]4[CH2:32][CH2:33][C@@H:27]3[CH2:28][CH:29]([N:34]3[C:38]5[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=5[N:36]=[C:35]3[CH3:43])[CH2:30]4)[CH2:20][CH2:19]2)[C:8]([O:10]CC2C=CC=CC=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[CH:1]1([CH:7]([N:18]2[CH2:23][CH2:22][C:21]([C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([F:50])[CH:45]=3)([CH2:24][CH2:25][N:26]3[C@H:27]4[CH2:33][CH2:32][C@@H:31]3[CH2:30][CH:29]([N:34]3[C:38]5[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=5[N:36]=[C:35]3[CH3:43])[CH2:28]4)[CH2:20][CH2:19]2)[C:8]([OH:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 68678071HCID 68678071, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68677588HCID 68677588, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl cyclohexyl(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)acetate (23.8 mg, 0.035 mmol) in 3 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 cyclohexyl(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)acetic acid (17.5 mg, 85%). ESI-MS 585 (M−H).

Workup

  1. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-216e2c93721d4ad1b67bcdb659ac0dd2
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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