(2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrile → (2S)-1-[[N-(4-methylbicyclo[2,2,2]oct-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile

HRID 2109493Notes

Reaction equation

[NH2:1][C:2]12[CH2:9][CH2:8][C:5]([CH3:10])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.Br[CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]#[N:21])=[O:14]>>[CH3:10][C:5]12[CH2:8][CH2:9][C:2]([NH:1][CH2:12][C:13]([N:15]3[CH2:19][CH2:18][CH2:17][C@H:16]3[C:20]#[N:21])=[O:14])([CH2:7][CH2:6]1)[CH2:3][CH2:4]2

Participants

Reactant 2

HCID 11031276(2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrile

HCID 131846104-Methylbicyclo[2.2.2]octan-1-amine

Product 1

HCID 57634356(2S)-1-[[N-(4-methylbicyclo[2,2,2]oct-1-yl)amino]acetyl]pyrrolidine-2-carbonitrileYield 60.2%

Procedure

Using 4-amino-1-methylbicyclo[2,2,2]octane (75.0 mg) and (2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrile (110 mg), the same procedure was followed as in Example 1 to obtain (2S)-1-[[N-(4-methylbicyclo[2,2,2]oct-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile (84.0 mg).

Sources & evidence

ORD record: ord-2f1f87da28bd491dbb00798e17e0b08c
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514571B2

Reaction notes

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