1-Piperidinecarboxylic acid, 3-(phenylmethoxy)-4-[(phenylmethyl)amino]-, ethyl ester, cis- → HCID 13677748, compound

HRID 846744Notes

Reaction equation

HRID 846744 reaction equation
C1(C[O:8][C@H:9]2[C@@H:14]([NH:15]CC3C=CC=CC=3)[CH2:13][CH2:12][N:11]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:10]2)C=CC=CC=1.[H][H]>[Pd].CO>[NH2:15][C@H:14]1[CH2:13][CH2:12][N:11]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:10][C@H:9]1[OH:8]

Participants

5

Reactant 2

HCID 136777451-Piperidinecarboxylic acid, 3-(phenylmethoxy)-4-[(phenylmethyl)amino]-, ethyl ester, cis-HCID 178418361HCID 178418361, compound

Product 1

HCID 13677748HCID 13677748, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 170 parts of ethyl cis-3-(phenylmethoxy)-4-[(phenylmethyl)amino]-1-piperidinecarboxylate and 400 parts of methanol was hydrogenated at normal pressure and at 80° C. with 20 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The oily residue was distilled, yielding 75 parts of ethyl cis-4-amino-3-hydroxy-1-piperidinecarboxylate; bp. 175°-185° C. at 0.4 mm. pressure. (intermediate 49).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. distillationThe oily residue was distilled

Sources & evidence

ORD record
ord-c089baa812e34ab9821a2cd46b52a834
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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