HCID 58442824, compound → 4-(2-Methoxycarbonylfuran-3-yl)piperidine-1-carboxylic acid t-butyl ester

HRID 41630Notes

Reaction equation

HRID 41630 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:18]=[CH:17][O:16][C:15]=2[C:19]([O:21][CH3:22])=[O:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:18]=[CH:17][O:16][C:15]=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 58442824HCID 58442824, compound

Product 1

HCID 584428164-(2-Methoxycarbonylfuran-3-yl)piperidine-1-carboxylic acid t-butyl esterYield 95.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(2-methoxycarbonylfuran-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (2.1 g, 6.8 mmol, 1.0 eq.) and Raney Ni (1.0 g) in MeOH (150 mL) was degassed and purged with hydrogen (3×). The mixture was hydrogenated (1 atm) for 2 days, then purged with nitrogen, filtered and washed with MeOH (50 mL). The filtrate was concentrated to yield 4-(2-methoxycarbonylfuran-3-yl)piperidine-1-carboxylic acid t-butyl ester (2.0 g) as a colorless oil.

Workup

  1. custompurged with hydrogen (3×)
  2. customfor 2 days
  3. custompurged with nitrogen
  4. filtrationfiltered
  5. washwashed with MeOH (50 mL)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c391212e34bf4180ad7e849c5b643900
Source dataset
uspto-grants-2013_09
Patent number
US08530663B2

Reaction notes

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