Potassium Iodide → Bisegliptin

HRID 606728Notes

Reaction equation

HRID 606728 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2.[F:22][C@@H:23]1[CH2:27][N:26]([C:28](=[O:40])[CH2:29]OS(C2C=CC=CC=2)(=O)=O)[C@H:25]([C:41]#[N:42])[CH2:24]1.[I-].[K+]>>[CH2:20]([O:19][C:17]([C:12]12[CH2:11][CH2:10][C:9]([NH:8][CH2:29][C:28]([N:26]3[CH2:27][C@@H:23]([F:22])[CH2:24][C@H:25]3[C:41]#[N:42])=[O:40])([CH2:16][CH2:15]1)[CH2:14][CH2:13]2)=[O:18])[CH3:21]

Participants

4

Reactant 3

HCID 4875Potassium IodideHCID 24781881(2S,4S)-1-[2-(benzenesulfonyloxy)acetyl]-4-fluoropyrrolidine-2-carbonitrileHCID 67053332Ethyl 4-aminobicyclo[2.2.2]octane-1-carboxylate 2,2,2-trifluoroacetate

Product 1

HCID 11688894BisegliptinYield 73%

Procedure

Using ethyl 4-aminobicyclo[2.2.2]octane-1-carboxylate trifluoroacetate (685 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 (511 mg, 73% yield). This compound was identical to the compound obtained in Example 7.

Sources & evidence

ORD record
ord-4a031de4d62447d39f68b4a3928f373d
Source dataset
uspto-grants-2011_03
Patent number
US07915427B2

Reaction notes

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