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

HRID 555678Notes

Reaction equation

HRID 555678 reaction equation
Br[CH2:2][C:3]([N:5]1[CH2:9][C@@H:8]([F:10])[CH2:7][C@H:6]1[C:11]#[N:12])=[O:4].Cl.F[C@@H]1CN[C@H](C(N)=O)C1.[Cl:23]CC(Cl)=O>>[Cl:23][CH2:2][C:3]([N:5]1[CH2:9][C@@H:8]([F:10])[CH2:7][C@H:6]1[C:11]#[N:12])=[O:4]

Participants

4

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 21090395(2S,4S)-1-(2-bromoacetyl)-4-fluoropyrrolidine-2-carbonitrileHCID 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 production process of (2S,4S)-1-(2-bromoacetyl)-4-fluoropyrrolidine-2-carbonitrile described in WO 02/38541 pamphlet, (2S,4S)-4-fluoropyrrolidine-2-carboxamide hydrochloride (5.00 g) and chloroacetyl chloride (2.60 mL) were used to obtain (2S,4S)-1-(2-chloroacetyl)-4-fluoropyrrolidine-2-carbonitrile (4.96 g).

Sources & evidence

ORD record
ord-e116ca2ca40c4176baaaca2d6564a690
Source dataset
uspto-grants-2011_11
Patent number
US08053465B2

Reaction notes

Loading…