Pyridine → HCID 131718969, compound

HRID 1654537Notes

Reaction equation

HRID 1654537 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([CH:13]1[S:17][CH2:16][NH:15][C@@H:14]1[C:18]([N:20]1[CH2:26][CH2:25][CH2:24][C@H:21]1[CH:22]=O)=[O:19])=[O:12].Cl.[NH2:28][OH:29].N1C=CC=CC=1>CN(C)C=O>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([CH:13]1[S:17][CH2:16][NH:15][C@@H:14]1[C:18]([N:20]1[CH2:26][CH2:25][CH2:24][C@H:21]1[CH:22]=[N:28][OH:29])=[O:19])=[O:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 131718968HCID 131718968, compound

Product 1

HCID 131718969HCID 131718969, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

1-[3-(Indan-2-ylacetyl)-L-thioprolyl]-L-prolinal (1.12 g), hydroxylamine hydrochloride salt (229 mg) and pyridine (266 μl) were dissolved in 10 ml of dimethylformamide, and stirred at 70° C. for 1.5 hours to obtain (2S)-1-[3-(indan-2-ylacetyl)-L-thioprolyl]-2-pyrrolidine aldoxime. Subsequently, 366 mg of selenium dioxide was added to the reaction solution, followed by agitation at 70° C. for 3 hours. The residue of selenium dioxide was filtered under aspiration, and the resulting filtrate was concentrated under reduced pressure. The residue was dissolved in 50 ml of methylene chloride, washed sequentially in 1N hydrochloric acid, saturated aqueous sodium chloride solution, and saturated aqueous sodium chloride solution, and dried over magnesium sulfate, followed by distillation of the solvent under reduced pressure. The resulting residue was purified by column chromatography to obtain 278 mg of (2S)-1-[3-(indan-2-yl-acetyl)-L-thioprolyl]-2-cyanopyrrolidine. Yield; 25%.

Sources & evidence

ORD record
ord-361c172cee90406292e7380f6e5b17ba
Source dataset
uspto-grants-1995_04
Patent number
US05407950

Reaction notes

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