HCID 58442808, compound → HCID 58442807, compound

HRID 41636Notes

Reaction equation

HRID 41636 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[O: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.[Ni]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O: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 58442808HCID 58442808, compound

Product 1

HCID 58442807HCID 58442807, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(3-methoxycarbonylfuran-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (0.8 g, 2.1 mmol, 1.0 eq.) and Raney Ni (0.4 g) in MeOH (50 mL) was degassed and purged with hydrogen (3×). The mixture was hydrogenated (1 atm) for 1 hour, then purged with nitrogen, filtered and washed with MeOH (15 mL). The filtrate was concentrated to yield 4-(3-methoxycarbonylfuran-2-yl)piperidine-1-carboxylic acid t-butyl ester (550 mg) as a white solid.

Workup

  1. custompurged with hydrogen (3×)
  2. customfor 1 hour
  3. custompurged with nitrogen
  4. filtrationfiltered
  5. washwashed with MeOH (15 mL)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-29393cf6798b4967bc166631619f25fc
Source dataset
uspto-grants-2013_09
Patent number
US08530663B2

Reaction notes

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