HCID 58442828, compound → 4-(3-Methoxycarbonylthiophen-2-yl)piperidine-1-carboxylic acid t-butyl ester

HRID 41650Notes

Reaction equation

HRID 41650 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[S:15][CH:16]=[CH:17][C:18]=2[C:19]([O:21][CH3:22])=[O:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][CH:16]=[CH:17][C:18]=2[C:19]([O:21][CH3:22])=[O:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 58442828HCID 58442828, compound

Product 1

HCID 584428224-(3-Methoxycarbonylthiophen-2-yl)piperidine-1-carboxylic acid t-butyl esterYield 75.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(3-methoxycarbonylthiophen-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (4.2 g, 13 mmol, 1.0 eq.) and Pd(OH)2/C (1.0 g, 1.4 mmol, 0.1 eq.) in MeOH (150 mL) was degassed and purged with hydrogen (3×). The mixture was hydrogenated (1 atm) at room temperature overnight, then the vessel was evacuated and purged with nitrogen, and the material was filtered and washed with MeOH (100 mL). The filtrate was concentrated then again allowed to hydrogenate at 1 atm at room temperature overnight. Filtering again as above, and concentrating the filtrate provided 4-(3-methoxycarbonylthiophen-2-yl)piperidine-1-carboxylic acid t-butyl ester (3.2 g) as a white solid.

Workup

  1. custompurged with hydrogen (3×)
  2. customat room temperature
  3. customovernight
  4. customthe vessel was evacuated
  5. custompurged with nitrogen
  6. filtrationthe material was filtered
  7. washwashed with MeOH (100 mL)
  8. concentrationThe filtrate was concentrated
  9. filtrationFiltering again as above, and
  10. concentrationconcentrating the filtrate

Sources & evidence

ORD record
ord-42b9226d5a624f928dc0a99207ef6005
Source dataset
uspto-grants-2013_09
Patent number
US08530663B2

Reaction notes

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