Methanol → 1-(tert-Butoxycarbonyl)-4-(pyridin-3-yl)piperidine-4-carboxylic acid

HRID 391456Notes

Reaction equation

HRID 391456 reaction equation
[C:1]([C:3]1([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#N.[OH-:22].[Na+].C[OH:25]>C(O)C>[C:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][C:3]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)([C:1]([OH:25])=[O:22])[CH2:4][CH2:5]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 14798Sodium HydroxideHCID 53793625tert-Butyl 4-cyano-4-(pyridin-3-yl)piperidine-1-carboxylate

Product 1

HCID 543822421-(tert-Butoxycarbonyl)-4-(pyridin-3-yl)piperidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A flask was charged with tert-butyl 4-cyano-4-(pyridin-3-yl)piperidine-1-carboxylate (7.5 g, 26.1 mmol) and NaOH (50% in water, 100 mL) in ethanol (100 ml) and heated at reflux for 6 h. The ethanol was removed, and the resulting solution was acidified to pH=5 using concentrated hydrochloric acid. The desired product was collected by filtration, and dried overnight to yield 4.1 g (51%). Mass Spec.: 307.18 (MH)+. LC tr=1.31 min (Phenomenex-Luna 4.6×50 mm S10, 10% MeOH/90% H2O/0.1% TFA→90% MeOH/10% H2O/0.1% TFA Gradient Time=2 min, Flow rate=4 mL/min)

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 h
  3. customThe ethanol was removed
  4. filtrationThe desired product was collected by filtration
  5. customdried overnight
  6. customto yield 4.1 g (51%)

Sources & evidence

ORD record
ord-8d7c8297fd454e6faad4471ee8232f60
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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