Chloroacetyl chloride → (2S,4S)-1-(2-Chloroacetyl)-4-fluoropyrrolidine-2-carbonitrile

HRID 227936Notes

Reaction equation

Cl.[F:2][C@@H:3]1[CH2:7][NH:6][C@H:5]([C:8]([NH2:10])=O)[CH2:4]1.[Cl:11][CH2:12][C:13](Cl)=[O:14]>>[Cl:11][CH2:12][C:13]([N:6]1[CH2:7][C@@H:3]([F:2])[CH2:4][C@H:5]1[C:8]#[N:10])=[O:14]

Participants

Reactant 2

HCID 6577Chloroacetyl chloride

HCID 451589172-Pyrrolidinecarboxamide, 4-fluoro-, hydrochloride (1:1), (2S,4S)-

Product 1

HCID 57518632(2S,4S)-1-(2-Chloroacetyl)-4-fluoropyrrolidine-2-carbonitrile

Procedure

According to the process for producing (2S,4S)-1-(2-bromoacetyl)-4-fluoropyrrolidine-2-carbonitrile described in the publication of WO 02/38541, (2S,4S)-4-fluoropyrrolidine-2-carboxamide hydrochloride (5.00 g) and chloroacetylchloride (2.60 mL) were used to give (2S,4S)-1-(2-chloroacetyl)-4-fluoropyrrolidine-2-carbonitrile (4.96 g).

Sources & evidence

ORD record: ord-e018549074524c8b9339c63a3b792c68
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560569B2

Reaction notes

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