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

HRID 555681Notes

Reaction equation

HRID 555681 reaction equation
[NH2:1][C:2]12[CH2:9][CH2:8][C:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.Br[CH2:18][C:19]([N:21]1[CH2:25][CH2:24][CH2:23][C@H:22]1[C:26]#[N:27])=[O:20]>>[C:13]([O:12][C:10]([C:5]12[CH2:4][CH2:3][C:2]([NH:1][CH2:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][C@H:22]3[C:26]#[N:27])=[O:20])([CH2:9][CH2:8]1)[CH2:7][CH2:6]2)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 11031276(2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrileHCID 23149669Tert-butyl 4-aminobicyclo(2.2.2)octane-1-carboxylate

Product 1

HCID 66987188(2S)-1-[[N-(4-t-butoxycarbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]pyrrolidine-2-carbonitrileYield 65.1%

Procedure

In a similar manner to Example 2, t-butyl 4-aminobicyclo[2.2.2]octane-1-carboxylate (100 mg) and (2S)-1-(2-bromoacetyl)pyrrolidine-2-carbonitrile (90.0 mg) were used to obtain (2S)-1-[[N-(4-t-butoxycarbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile (97.6 mg).

Sources & evidence

ORD record
ord-4daf744fe9e445d88c19910272f20dee
Source dataset
uspto-grants-2011_11
Patent number
US08053465B2

Reaction notes

Loading…