(2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrile → (2S)-1-[[N-(4-ethoxycarbonylbicyclo[2.2.1]hept-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile

HRID 555685Notes

Reaction equation

HRID 555685 reaction equation
[NH2:1][C:2]12[CH2:8][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.Br[CH2:15][C:16]([N:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[C:23]#[N:24])=[O:17]>>[CH2:12]([O:11][C:9]([C:5]12[CH2:8][C:2]([NH:1][CH2:15][C:16]([N:18]3[CH2:22][CH2:21][CH2:20][C@H:19]3[C:23]#[N:24])=[O:17])([CH2:3][CH2:4]1)[CH2:7][CH2:6]2)=[O:10])[CH3:13]

Participants

3

Reactant 2

HCID 11031276(2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrileHCID 23149671Ethyl 4-aminobicyclo[2.2.1]heptane-1-carboxylate

Product 1

HCID 59383138(2S)-1-[[N-(4-ethoxycarbonylbicyclo[2.2.1]hept-1-yl)amino]acetyl]pyrrolidine-2-carbonitrileYield 91.1%

Procedure

In a similar manner to Example 6, ethyl 4-aminobicyclo[2.2.1]heptane-1-carboxylate (50.0 mg) and (2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrile (59.3 mg) were used to obtain (2S)-1-[[N-(4-ethoxycarbonylbicyclo[2.2.1]hept-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile (79.4 mg).

Sources & evidence

ORD record
ord-b9bdc4e66f354c6fb47bb9eab3e2e0de
Source dataset
uspto-grants-2011_11
Patent number
US08053465B2

Reaction notes

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