Aniline → (R)-1-Boc-piperidine-3-carboxylic acid phenylamide

HRID 1246896Notes

Reaction equation

HRID 1246896 reaction equation
[C:1]([N:8]1[CH2:16][CH2:15][CH2:14][C@@H:10]([C:11]([OH:13])=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:18]1([NH:17][C:11]([C@@H:10]2[CH2:14][CH2:15][CH2:16][N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:9]2)=[O:13])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 10868DicyclohexylcarbodiimideHCID 6435161-(1,1-Dimethylethyl) (3R)-1,3-piperidinedicarboxylate

Product 1

HCID 54303026(R)-1-Boc-piperidine-3-carboxylic acid phenylamideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-Boc-(R)-nipecotic acid 25 (4.00 g, 17.5 mmol) and aniline (1.67 mL, 1.05 eq.) in 30 mL of dry CH2Cl2 was added DCC (4.88 g, 1.05 eq.) in one portion at 0° C. The mixture was stirred at room temperature for 4 hours. Filtration and removal of the solvent gave an oily crude product, which was purified by flash column chromatography (silica gel, hexane:ethyl acetate) to afford (R)-1-Boc-piperidine-3-carboxylic acid phenyl amide 26 as a colorless oil (5.26 g, 99%).

Workup

  1. filtrationFiltration and removal of the solvent
  2. customgave an oily crude product, which
  3. customwas purified by flash column chromatography (silica gel, hexane:ethyl acetate)

Sources & evidence

ORD record
ord-f986cc7616da457e9420f7c0b6d7b00f
Source dataset
uspto-grants-2006_10
Patent number
US07129228B2

Reaction notes

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