Potassium Iodide → Bisegliptin

HRID 606729Notes

Reaction equation

HRID 606729 reaction equation
CS(O)(=O)=O.[NH2:6][C:7]12[CH2:14][CH2:13][C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])([CH2:11][CH2:12]1)[CH2:9][CH2:8]2.[F:20][C@@H:21]1[CH2:25][N:24]([C:26](=[O:38])[CH2:27]OS(C2C=CC=CC=2)(=O)=O)[C@H:23]([C:39]#[N:40])[CH2:22]1.[I-].[K+]>>[CH2:18]([O:17][C:15]([C:10]12[CH2:9][CH2:8][C:7]([NH:6][CH2:27][C:26]([N:24]3[CH2:25][C@@H:21]([F:20])[CH2:22][C@H:23]3[C:39]#[N:40])=[O:38])([CH2:14][CH2:13]1)[CH2:12][CH2:11]2)=[O:16])[CH3:19]

Participants

4

Reactant 3

HCID 4875Potassium IodideHCID 24781881(2S,4S)-1-[2-(benzenesulfonyloxy)acetyl]-4-fluoropyrrolidine-2-carbonitrileHCID 86627921Ethyl 4-aminobicyclo[2.2.2]octane-1-carboxylate methanesulfonate

Product 1

HCID 11688894BisegliptinYield 79%

Procedure

Using ethyl 4-aminobicyclo[2.2.2]octane-1-carboxylate methanesulfonate (645 mg), (2S,4S)-4-fluoro-1-[2-(benzenesulfonyloxy)acetyl]pyrrolidine-2-carbonitrile (625 mg) and potassium iodide (33.2 mg), the same procedure was followed as in Example 7 to give (2S,4S)-1-[2-[(4-ethoxycarbonylbicyclo[2.2.2]oct-1-yl)amino]ac etyl]-4-fluoropyrrolidine-2-carbonitrile (553 mg, 79% yield). This compound was identical to the compound obtained in Example 7.

Sources & evidence

ORD record
ord-535ff205503745a9b250890e1cac53f0
Source dataset
uspto-grants-2011_03
Patent number
US07915427B2

Reaction notes

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