(2S)-Pyrrolidine-2-carbonitrile hydrochloride → HCID 67506428, compound

HRID 1791898Notes

Reaction equation

HRID 1791898 reaction equation
[C:1]([NH:9][C@H:10]1[CH2:14][N:13](C(OC(C)(C)C)=O)[C@H:12]([C:22]([OH:24])=O)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:25].[C:26]([C@@H:28]1[CH2:32][CH2:31][CH2:30][NH:29]1)#[N:27]>CN(C=O)C>[ClH:25].[C:1]([NH:9][C@H:10]1[CH2:14][NH:13][C@H:12]([C:22]([N:29]2[CH2:30][CH2:31][CH2:32][C@H:28]2[C:26]#[N:27])=[O:24])[CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 44593801(2S)-Pyrrolidine-2-carbonitrile hydrochlorideHCID 67506184HCID 67506184, compound

Product 1

HCID 67506428HCID 67506428, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2S,4R)-4-Benzoylamino-1-tert-butoxycarbonylpyrrolidine-2-carboxylic acid (title compound of Reference Example 8, 1.6 g) and (S)-2-cyanopyrrolidine hydrochloride (0.63 g) were dissolved in DMF (10 mL), and triethylamine (1.32 mL), HOBT (0.79 g) and EDC hydrochloride (0.99 g) were successively added. The mixture was stirred at room temperature for 15 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was dried and evaporated under reduced pressure. The residue was purified by silica gel chromatography to give (S)-1-((2S,4R)-4-benzoylamino-1-tert-butoxycarbonyl-2-pyrrolidinylcarbonyl)-2-cyanopyrrolidine (1.2 g) as a white solid.

Sources & evidence

ORD record
ord-defa255eef994bfa94bf4e3fc64a8ca9
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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