2-Chloro-4-fluorobenzonitrile → 2-chloro-4-[(2S,3S)-3-hydroxy-2-methylpyrrolidin-1-yl]benzonitrile

Reaction equation

[OH:1][C@@H:2]1[C@H:6]([CH3:7])[NH:5][C:4](=O)[CH2:3]1.[Cl:9][C:10]1[CH:17]=[C:16](F)[CH:15]=[CH:14][C:11]=1[C:12]#[N:13]>>[Cl:9][C:10]1[CH:17]=[C:16]([N:5]2[CH2:4][CH2:3][C@H:2]([OH:1])[C@@H:6]2[CH3:7])[CH:15]=[CH:14][C:11]=1[C:12]#[N:13]

Participants

Reactant 2

HCID 1090002-Chloro-4-fluorobenzonitrile

HCID 11062347(4S,5S)-4-hydroxy-5-methylpyrrolidin-2-one

Product 1

HCID 593705202-chloro-4-[(2S,3S)-3-hydroxy-2-methylpyrrolidin-1-yl]benzonitrile

Procedure

Using (4S,5S)-4-hydroxy-5-methylpyrrolidin-2-one and 2-chloro-4-fluorobenzonitrile as starting materials, the title compound was obtained by the same manner as shown in Example 2 (reaction time 1 hr).

Sources & evidence

ORD record: ord-66a5f6798ab74855912cef7727e4955c
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592452B2

Reaction notes

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