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

HRID 2166927Notes

Reaction equation

HRID 2166927 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-23ea5d759b5142f8b4a7cbfa54b55cbc
Source dataset
uspto-grants-1983_06
Patent number
US04390695

Reaction notes

Loading…