Bromomethylcyclopropane → HCID 59383134, compound

HRID 2355181Notes

Reaction equation

[C:1]([C:4]12[CH2:11][CH2:10][C:7]([NH:12][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])([CH2:8][CH2:9]1)[CH2:6][CH2:5]2)([OH:3])=[O:2].[CH:24]1([CH2:27]Br)[CH2:26][CH2:25]1>>[CH:24]1([CH2:27][O:2][C:1]([C:4]23[CH2:11][CH2:10][C:7]([NH:12][CH2:13][C:14]([N:16]4[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]4[C:22]#[N:23])=[O:15])([CH2:8][CH2:9]2)[CH2:6][CH2:5]3)=[O:3])[CH2:26][CH2:25]1

Participants

Reactant 2

HCID 81503Bromomethylcyclopropane

HCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 59383134HCID 59383134, compoundYield 58.7%

Procedure

In a similar manner to Example 8, (2S,4S)-1-[[N-(4-carboxybicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (20.0 mg) and cyclopropylmethyl bromide (12.8 mg) were used to obtain (2S,4S)-1-[[N-(4-cyclopropylmethyloxycarbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (13.7 mg).

Sources & evidence

ORD record: ord-185f630ae1244c84ae660b8d0d671036
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754757B2

Reaction notes

Loading…