(2S,4S)-1-[2-(benzenesulfonyloxy)acetyl]-4-fluoropyrrolidine-2-carbonitrile → Bisegliptin

HRID 606727Notes

Reaction equation

HRID 606727 reaction equation
C1(S(O)(=O)=O)C=CC=CC=1.[NH2:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2.[F:25][C@@H:26]1[CH2:30][N:29]([C:31](=[O:43])[CH2:32]OS(C2C=CC=CC=2)(=O)=O)[C@H:28]([C:44]#[N:45])[CH2:27]1>>[CH2:23]([O:22][C:20]([C:15]12[CH2:14][CH2:13][C:12]([NH:11][CH2:32][C:31]([N:29]3[CH2:30][C@@H:26]([F:25])[CH2:27][C@H:28]3[C:44]#[N:45])=[O:43])([CH2:19][CH2:18]1)[CH2:17][CH2:16]2)=[O:21])[CH3:24]

Participants

3

Reactant 2

HCID 24781881(2S,4S)-1-[2-(benzenesulfonyloxy)acetyl]-4-fluoropyrrolidine-2-carbonitrileHCID 86627920Ethyl 4-aminobicyclo[2.2.2]octane-1-carboxylate benzenesulfonate

Product 1

HCID 11688894BisegliptinYield 101.1%

Procedure

Using ethyl 4-aminobicyclo[2.2.2]octane-1-carboxylate benzenesulfonate (609 mg) and (2S,4S)-4-fluoro-1-[2-(benzenesulfonyloxy)acetyl]pyrrolidine-2-carbonitrile (783 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 (609 mg, 87% yield). This compound was identical to the compound obtained in Example 7.

Sources & evidence

ORD record
ord-e2083035ba624bbf9308231e3dbc53ac
Source dataset
uspto-grants-2011_03
Patent number
US07915427B2

Reaction notes

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