Chloroacetyl chloride → (R)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile

HRID 1393638Notes

Reaction equation

[NH:1]1[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([NH2:5])=O.[Cl:9][CH2:10][C:11](Cl)=[O:12]>>[Cl:9][CH2:10][C:11]([N:1]1[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]#[N:5])=[O:12]

Participants

Reactant 2

HCID 6577Chloroacetyl chloride

HCID 447554Prolinamide, D-

Product 1

HCID 10920982(R)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrileYield 66%

Procedure

In a similar procedure as employed in the Intermediate Example 1, D-proline amide (3.2 g) was reacted with chloroacetyl chloride (2.5 ml) and then subjected to dehydration reaction to give the title compound (3.2 g, Y.:66%).

Workup

customsubjected to dehydration reaction

Sources & evidence

ORD record: ord-97529f24edb74ab6b26e94f4daf428a6
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07345180B2

Reaction notes

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