Piperidine-2-carboxylic acid tert-butylamide → 1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-2(S)-piperidinecarboxamide

HRID 742862Notes

Reaction equation

HRID 742862 reaction equation
[C:1]([NH:5][C:6]([C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:21][C:22]([NH:24][C@@H:25]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C@@H:26]1[O:28][CH2:27]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[CH2:14]([O:21][C:22]([NH:24][C@@H:25]([CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C@H:26]([OH:28])[CH2:27][N:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@H:8]1[C:6]([NH:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:23])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 5289197Piperidine-2-carboxylic acid tert-butylamideHCID 9861019(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

Product 1

HCID 569781971-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-2(S)-piperidinecarboxamideYield 91.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.576 g of N-tert.butyl-2(S)-piperidinecarboxamide and 4.158 g of 3(S)-(benzyloxyformamido)-1,2(S)-epoxy-4-phenylbutane in 70 ml of ethanol was heated at reflux for 16 hours. The solvent was removed by evaporation and the residue was dissolved in 100 ml of diethyl ether and treated with 10 g of activated magnesium silicate. The solvent was then removed by evaporation and there were obtained 6.16 g of 1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-2(S)-piperidinecarboxamide as a colourless glass; MS: m/e 482 [M+H]+.

Workup

  1. temperatureat reflux for 16 hours
  2. customThe solvent was removed by evaporation
  3. dissolutionthe residue was dissolved in 100 ml of diethyl ether
  4. additiontreated with 10 g of activated magnesium silicate
  5. customThe solvent was then removed by evaporation

Sources & evidence

ORD record
ord-db32f9ef3ca941f08903d1a914c749aa
Source dataset
uspto-grants-1996_09
Patent number
US05554756

Reaction notes

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