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

HRID 483230Notes

Reaction equation

HRID 483230 reaction equation
[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:19][C@H:18](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:17][C@H:12]2[C:13]([O:15][CH3:16])=[O:14])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>>[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:19][C@@H:18]([N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:17][C@H:12]2[C:13]([O:15][CH3:16])=[O:14])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 391525Zofenopril Impurity 4

Product 1

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

Procedure

A mixture of 15.0 g of 1-[(phenylmethoxy)carbonyl]-trans-4-tosyloxy-L-proline, methyl ester (J.A.C.S., 79, 191 (1957)) and 75 ml of piperidine is stirred at room temperature for 24 hours. The excess piperidine is removed under reduced pressure and the residue is dissolved in 50 ml of chloroform. The latter solution is extracted twice with 10 ml portions of water, dried (MgSO4), filtered and the solvent evaporated to give the title compound.

Workup

  1. customThe excess piperidine is removed under reduced pressure
  2. dissolutionthe residue is dissolved in 50 ml of chloroform
  3. extractionThe latter solution is extracted twice with 10 ml portions of water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-29d1abdeb20843a39b95d15f13b0b0f0
Source dataset
uspto-grants-1986_03
Patent number
US04578474

Reaction notes

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