1-(1,1-Dimethylethyl) 2-ethyl 4-(cyanomethylene)-1,2-piperidinedicarboxylate → ethyl cis-4-cyanomethyl-N-t-butoxycarbonyl-2-piperidinecarboxylate

HRID 1073091Notes

Reaction equation

HRID 1073091 reaction equation
[C:1]([CH:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:5]1)#[N:2]>C(O)C.[Pd]>[C:1]([CH2:3][C@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[C@@H:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:5]1)#[N:2]

Participants

4

Reactant 1

HCID 542786301-(1,1-Dimethylethyl) 2-ethyl 4-(cyanomethylene)-1,2-piperidinedicarboxylate

Product 1

HCID 15928264ethyl cis-4-cyanomethyl-N-t-butoxycarbonyl-2-piperidinecarboxylateYield 89.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 4-cyanomethylidene-N-t-butoxycarbonyl-2-piperidinecarboxylate (9.00 g, 0.031 mol) was hydrogenated in 140 ml of ethanol with 0.90 g of 5% by weight palladium-on-carbon at room temperature and 60 p.s.i. for 60 minutes. The mixture was filtered through Celite and concentrated under vacuum. High pressure liquid chromatography of the residue provided 8.20 g of ethyl cis-4-cyanomethyl-N-t-butoxycarbonyl-2-piperidinecarboxylate.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7d356267136e41eb9b2bc10574d96653
Source dataset
uspto-grants-1990_11
Patent number
US04968678

Reaction notes

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