[4S]-1-[(Phenylmethoxy)carbonyl]-4-(1-piperidinyl)-L-proline, methyl ester → [4S]-4-(1-Piperidinyl)-L-proline, methyl ester

HRID 483231Notes

Reaction equation

HRID 483231 reaction equation
C1(COC([N:11]2[CH2:19][C@@H:18]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:17][C@H:12]2[C:13]([O:15][CH3:16])=[O:14])=O)C=CC=CC=1.[H][H]>CO.[Pd].O>[N:20]1([C@@H:18]2[CH2:19][NH:11][C@H:12]([C:13]([O:15][CH3:16])=[O:14])[CH2:17]2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

6

Reactant 2

HCID 131712640[4S]-1-[(Phenylmethoxy)carbonyl]-4-(1-piperidinyl)-L-proline, methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 131712641[4S]-4-(1-Piperidinyl)-L-proline, methyl ester

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 10.0 g of [4S]-1-[(phenylmethoxy)carbonyl]-4-(1-piperidinyl)-L-proline, methyl ester in 100 ml of methanol is treated with a suspension of 2 g of 5% palladium on charcoal in 10 ml of water and placed under 3 atmospheres of hydrogen. After an equivalent quantity of hydrogen is consumed, the suspension is filtered and the solvent evaporated to give the title compound.

Workup

  1. customAfter an equivalent quantity of hydrogen is consumed
  2. filtrationthe suspension is filtered
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-24788e3d35ad4bae8a7257db8562ef31
Source dataset
uspto-grants-1986_03
Patent number
US04578474

Reaction notes

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