(2S)-2-((3R)-3-(4-(2-methoxyphenyl)piperidin-1-yl)-2-cyclopropylpyrrolidin-1-yl)-2-phenylethanol → 1-((3R)-2-cyclopropylpyrrolidin-3-yl)-4-(2-methoxyphenyl)piperidine

HRID 406491Notes

Reaction equation

HRID 406491 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][N:12]([C@@H:15]2[CH2:19][CH2:18][N:17]([C@@H](C3C=CC=CC=3)CO)[CH:16]2[CH:29]2[CH2:31][CH2:30]2)[CH2:11][CH2:10]1>CCO.[OH-].[OH-].[Pd+2]>[CH:29]1([CH:16]2[C@H:15]([N:12]3[CH2:11][CH2:10][CH:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])[CH2:14][CH2:13]3)[CH2:19][CH2:18][NH:17]2)[CH2:30][CH2:31]1

Participants

4

Reactant 1

HCID 59764970(2S)-2-((3R)-3-(4-(2-methoxyphenyl)piperidin-1-yl)-2-cyclopropylpyrrolidin-1-yl)-2-phenylethanol

Product 1

HCID 597648261-((3R)-2-cyclopropylpyrrolidin-3-yl)-4-(2-methoxyphenyl)piperidineYield 100.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of (2S)-2-((3R)-3-(4-(2-methoxyphenyl)piperidin-1-yl)-2-cyclopropylpyrrolidin-1-yl)-2-phenylethanol (preparation #26) (1.708 g, 4.06 mmol) in EtOH (25 mL) was hydrogenated under hydrogen at about 60 bar at about 60° C. in a H-cube™ apparatus using palladium hydroxide on carbon (20%) as a catalyst until all starting material was converted to product. The solvent was removed in vacuo to afford 1-((3R)-2-cyclopropylpyrrolidin-3-yl)-4-(2-methoxyphenyl)piperidine (1.23 g, 4.09 mmol) as an orange oil. RP-HPLC (Table 1, Method a) Rt 1.48 min; m/z: (M+H)+ 301.

Workup

  1. customwas hydrogenated under hydrogen at about 60 bar at about 60° C. in a H-cube™ apparatus
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-18cd7e49fe6842828185969083334b10
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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