Dicyclohexylcarbodiimide → 3-Phenyl-1,2,3,6-tetrahydropyridine-2-carboxamide

HRID 343625Notes

Reaction equation

HRID 343625 reaction equation
COC1C=CC(S([N:12]2[CH2:17][CH:16]=[CH:15][C@H:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@@H:13]2[C:24]([OH:26])=O)(=O)=O)=CC=1.Cl.C([NH:35]O)C1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C>C(OCC)(=O)C>[C:18]1([CH:14]2[CH:15]=[CH:16][CH2:17][NH:12][CH:13]2[C:24]([NH2:35])=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 11332622N-benzylhydroxylamine hydrochlorideHCID 53762982(+)-(2R*-3R*)-1-(4-methoxybenzenesulfonyl)-3-phenyl-1,2,3,6-tetrahydropyridine-2-carboxylic acid

Product 1

HCID 867536203-Phenyl-1,2,3,6-tetrahydropyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (+)-(2R*-3R*)-1-(4-methoxybenzenesulfonyl)-3-phenyl-1,2,3,6-tetrahydropyridine-2-carboxylic acid (65 mg, 0.17 mmol) (from Example 20), is added benzylhydroxylamine hydrochloride (32 mg, 0.20 mmol), dicyclohexylcarbodiimide (41 mg, 0.20 mmol) and dimethylaminopyridine (27 mg, 0.22 mmol). The resulting mixture is stirred overnight, diluted with ethyl acetate and filtered through Celite™ and evaporated. The crude product is purified by chromatography elution with 1:1 hexane-ethyl acetate to provide (+)-(2R*-3R*)-N-benzyloxy-1-4-methoxybenzenesulfonyl)-3-phenyl-1,2,3,6-tetrahydropyridine-2-carboxamide.

Workup

  1. filtrationfiltered through Celite™
  2. customevaporated
  3. customThe crude product is purified by chromatography elution with 1:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-d97b5ecf44ea4ea8a752115ea2ecced7
Source dataset
uspto-grants-1999_01
Patent number
US05861510

Reaction notes

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