Sodium Hydroxide → HCID 67125860, compound

HRID 929965Notes

Reaction equation

HRID 929965 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([O:23]C)=[O:22])=[N:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([OH:23])=[O:22])=[N:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67125926HCID 67125926, compound

Product 1

HCID 67125860HCID 67125860, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)methyl)picolinate (200 mg, 0.60 mmol) was stirred at rt in THF/MeOH (1:1, v/v). 3N NaOH (0.2 mL, 0.60 mmol) was added and the resulting mixture was stirred at rt for 5 h. TLC indicated the reaction was complete. Most of the volatile solvent was evaporated under reduced pressure. The residue was acidified with 3N aq. HCl to pH˜5, and extracted with DCM (2×20 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to give 5-((1-(tert-butoxycarbonyl)piperidin-4-yl)methyl)picolinic acid as a white semi-solid (200 mg, quantitative).

Workup

  1. customMost of the volatile solvent was evaporated under reduced pressure
  2. extractionextracted with DCM (2×20 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7b6c12ac4bff4736b7074b58500ecb55
Source dataset
uspto-grants-2016_03
Patent number
US09296722B2

Reaction notes

Loading…