2-Nitrobenzenesulfonyl chloride → (2S,4S)-4-fluoro-1-[2-[(2-nitrophenyl)sulfonyloxy]acetyl]pyrro lidine-2-carbonitrile

HRID 606717Notes

Reaction equation

HRID 606717 reaction equation
[F:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:10])[CH2:8][OH:9])[C@H:4]([C:11]#[N:12])[CH2:3]1.[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22](Cl)(=[O:24])=[O:23])([O-:15])=[O:14]>>[F:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:10])[CH2:8][O:9][S:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N+:13]([O-:15])=[O:14])(=[O:23])=[O:24])[C@H:4]([C:11]#[N:12])[CH2:3]1

Participants

3

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 67053346(2S,4S)-4-fluoro-1-(2-hydroxyacetyl)pyrrolidine-2-carbonitrile

Product 1

HCID 86627919(2S,4S)-4-fluoro-1-[2-[(2-nitrophenyl)sulfonyloxy]acetyl]pyrro lidine-2-carbonitrileYield 15.1%

Procedure

Using (2S,4S)-4-fluoro-1-(2-hydroxyacetyl)pyrrolidine-2-carbonitrile (259 mg) and 2-nitrobenzenesulfonyl chloride (366 mg), the same procedure was followed as in Reference Example 3 to give (2S,4S)-4-fluoro-1-[2-[(2-nitrophenyl)sulfonyloxy]acetyl]pyrro lidine-2-carbonitrile as a pale yellow solid (81.2 mg, 15% yield).

Sources & evidence

ORD record
ord-7a2f95d21fa941968f5a662a205dc2da
Source dataset
uspto-grants-2011_03
Patent number
US07915427B2

Reaction notes

Loading…