Hydroxide → 4-(4-Carboxy-thiophen-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 1809099Notes

Reaction equation

HRID 1809099 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]([O:21]CC)=[O:20])[CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na].[OH-]>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]([OH:21])=[O:20])[CH:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 961HydroxideHCID 5360545SodiumHCID 595425874-(4-Ethoxycarbonyl-thiophen-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 595425244-(4-Carboxy-thiophen-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl esterYield 50.6%

Conditions

Temperature
130 °C

Procedure

4-(4-Ethoxycarbonyl-thiophen-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (1.0 g, 3 mmol) was dissolved in IMS (10 mL) and aqueous sodium ,hydroxide (1 M, 8 mmol) was added and the mixture stirred at 130° C. for 10 minutes. The solution was then cooled, filtered and acidified with 1 N hydrochloric acid to pH 4. The resulting precipitate was isolated by filtration and dried under vacuum to give the title compound as a white solid (0.47 g). LCMS m/z 308.48 [M−H]− RT=3.45 min (Analytical Method 4).

Workup

  1. temperatureThe solution was then cooled
  2. filtrationfiltered
  3. customThe resulting precipitate was isolated by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-32747303a5e04edb8b34df6d1656e303
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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