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

HRID 2109495Notes

Reaction equation

HRID 2109495 reaction equation
[NH2:1][C:2]12[CH2:9][CH2:8][C:5]([CH2:10][OH:11])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.Br[CH2:13][C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]#[N:22])=[O:15]>>[OH:11][CH2:10][C:5]12[CH2:8][CH2:9][C:2]([NH:1][CH2:13][C:14]([N:16]3[CH2:20][CH2:19][CH2:18][C@H:17]3[C:21]#[N:22])=[O:15])([CH2:3][CH2:4]1)[CH2:7][CH2:6]2

Participants

3

Reactant 2

HCID 11031276(2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrileHCID 23152950{4-Aminobicyclo[2.2.2]octan-1-yl}methanol

Product 1

HCID 57634357(2S)-1-[[N-(4-hydroxymethylbicyclo[2,2,2]oct-1-yl)amino]acetyl]pyrrolidine-2-carbonitrileYield 68.8%

Procedure

Using 4-amino-1-hydroxymethylbicyclo[2,2,2]octane (50.5 mg) and (2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrile (61.7 mg), the same procedure was followed as in Example 5 to obtain (2S)-1-[[N-(4-hydroxymethylbicyclo[2,2,2]oct-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile (57.0 mg).

Sources & evidence

ORD record
ord-d0e3322c4057427fbd46d7333aa6cdd1
Source dataset
uspto-grants-2009_04
Patent number
US07514571B2

Reaction notes

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