1,1-Dimethylethyl 4-(3-cyanophenyl)-4-hydroxy-1-piperidinecarboxylate → HCID 22266143, compound

HRID 489608Notes

Reaction equation

HRID 489608 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=2)([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>N.CO.[Rh]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH2:22])[CH:16]=2)([OH:14])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 222661661,1-Dimethylethyl 4-(3-cyanophenyl)-4-hydroxy-1-piperidinecarboxylate

Product 1

HCID 22266143HCID 22266143, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 21705897Ammonia methanolSolvent

Procedure

A solution of 4-(3-Cyano-phenyl)-4-hydroxy-piperidine-1-carboxylic acid-tert-butyl ester (0.30 g, 0.99 mmol) in 7N ammonia/methanol (25 mL) and 5%Rhodium on alumina (0.15 g) was hydrogenated overnight on a Parr apparatus (45 psi). The reaction was filtered through celite, evaporated, and azeotroped with MeOH:toluene 1:1 (2×30 mL) to give 4-(3-Aminomethyl-phenyl)-4-hydroxy-piperidine-1-carboxylic acid-tert-butyl ester as a foam. This compound was used directly in the next step.

Workup

  1. filtrationThe reaction was filtered through celite
  2. customevaporated
  3. customazeotroped with MeOH:toluene 1:1 (2×30 mL)

Sources & evidence

ORD record
ord-15e0be7b823045e4afc3ee73fcc58c36
Source dataset
uspto-grants-2005_12
Patent number
US06977263B2

Reaction notes

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