Methanol → HCID 58442821, compound

HRID 41646Notes

Reaction equation

HRID 41646 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][S:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][S:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 58442820HCID 58442820, compound

Product 1

HCID 58442821HCID 58442821, compoundYield 49.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(4-methoxycarbonylthiophen-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (200 mg, 620 μmol, 1.0 eq.) in EtOAc (25 mL) was combined with Pd(OH)2/C (70 mg) under hydrogen (1 atm). MeOH (10 mL) was added and the resulting solution was stirred for 20 hours at room temperature. The solution was then stirred for an additional 16 hours while the temperature was maintained at 40° C. in an oil bath. The solids were filtered and the filtrate was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with EtOAc/PE (1:20) to yield 4-(4-methoxycarbonylthiophen-3-yl)-piperidine-1-carboxylic acid t-butyl ester (0.1 g) as a colorless oil.

Workup

  1. stirringThe solution was then stirred for an additional 16 hours while the temperature
  2. temperaturewas maintained at 40° C. in an oil bath
  3. filtrationThe solids were filtered
  4. concentrationthe filtrate was concentrated under vacuum
  5. washeluted with EtOAc/PE (1:20)

Sources & evidence

ORD record
ord-84259b41df0e4a7fb18721e7cbd90177
Source dataset
uspto-grants-2013_09
Patent number
US08530663B2

Reaction notes

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