Hydrochloric Acid → (S)-methyl 5-(2-oxo-1-(piperidin-4-yl)pyrrolidin-3-yloxy)picolinate hydrochloride

HRID 407991Notes

Reaction equation

HRID 407991 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH2:19][CH2:18][C@H:17]([O:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]([O:29][CH3:30])=[O:28])=[N:25][CH:26]=3)[C:16]2=[O:31])[CH2:11][CH2:10]1)=O)(C)(C)C>CO>[ClH:1].[O:31]=[C:16]1[C@@H:17]([O:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]([O:29][CH3:30])=[O:28])=[N:25][CH:26]=2)[CH2:18][CH2:19][N:15]1[CH:12]1[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67469865(S)-methyl 5-(1-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-oxopyrrolidin-3-yloxy)picolinate

Product 1

HCID 67469702(S)-methyl 5-(2-oxo-1-(piperidin-4-yl)pyrrolidin-3-yloxy)picolinate hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated aqueous HCl (2 mL) was added to a suspension of (S)-methyl 5-(1-(1-(tert-butoxycarbonyl)piperidin-4-yl)-2-oxopyrrolidin-3-yloxy)picolinate (0.19 g, 0.45 mmol) in MeOH (4 mL). The mixture was stirred at ambient temperature overnight and then concentrated. The residue was concentrated from MeOH twice to afford (S)-methyl 5-(2-oxo-1-(piperidin-4-yl)pyrrolidin-3-yloxy)picolinate hydrochloride (0.19 g, 0.44 mmol, 98%).

Workup

  1. concentrationconcentrated
  2. concentrationThe residue was concentrated from MeOH twice

Sources & evidence

ORD record
ord-c522d26109f9429ab6e9a6097fadb3e0
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

Loading…