(2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrile → (2S)-1-[[(4-carbamoylbicyclo[2.2.2]oct-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile

HRID 227938Notes

Reaction equation

[NH2:1][C:2]12[CH2:9][CH2:8][C:5]([C:10]([NH2:12])=[O:11])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.Br[CH2:14][C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[C:22]#[N:23])=[O:16]>>[C:10]([C:5]12[CH2:4][CH2:3][C:2]([NH:1][CH2:14][C:15]([N:17]3[CH2:21][CH2:20][CH2:19][C@H:18]3[C:22]#[N:23])=[O:16])([CH2:9][CH2:8]1)[CH2:7][CH2:6]2)(=[O:11])[NH2:12]

Participants

Reactant 2

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

HCID 231505304-Aminobicyclo[2.2.2]octane-1-carboxamide

Product 1

HCID 57756756(2S)-1-[[(4-carbamoylbicyclo[2.2.2]oct-1-yl)amino]acetyl]pyrrolidine-2-carbonitrileYield 59.5%

Procedure

Using 4-aminobicyclo[2.2.2]octane-1-carboxamide (50.0 mg) and (2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrile (56.9 mg), the same procedure was followed as in Example 1 to give (2S)-1-[[(4-carbamoylbicyclo[2.2.2]oct-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile (47.5 mg).

Sources & evidence

ORD record: ord-5c1122efecf746319f65723b16a3fa5c
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560569B2

Reaction notes

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