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

HRID 2109494Notes

Reaction equation

HRID 2109494 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][C@@H:19]([F:21])[CH2:18][C@H:17]1[C:22]#[N:23])=[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][C@@H:19]([F:21])[CH2:18][C@H:17]3[C:22]#[N:23])=[O:15])([CH2:3][CH2:4]1)[CH2:7][CH2:6]2

Participants

3

Reactant 2

HCID 21090395(2S,4S)-1-(2-bromoacetyl)-4-fluoropyrrolidine-2-carbonitrileHCID 23152950{4-Aminobicyclo[2.2.2]octan-1-yl}methanol

Product 1

HCID 57634358(2S,4S)-1-[[N-(4-hydroxymethylbicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrileYield 93.3%

Procedure

Using 4-amino-1-hydroxymethylbicyclo[2,2,2]octane (50.0 mg) and (2S,4S)-1-(2-bromoacetyl)-4-fluoropyrrolidine-2-carbonitrile (75.7 mg), the same procedure was followed as in Example 5 to obtain (2S,4S)-1-[[N-(4-hydroxymethylbicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (93.0 mg).

Sources & evidence

ORD record
ord-284ddc4cb2d941adb61ed3b4abcfde5a
Source dataset
uspto-grants-2009_04
Patent number
US07514571B2

Reaction notes

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