Potassium Carbonate → (S)-tert-butyl 4-(3-(1H-indazol-5-yloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

HRID 407966Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([OH:10])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.CS(O[C@@H:16]1[CH2:20][CH2:19][N:18]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[C:17]1=[O:34])(=O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C@H:16]3[CH2:20][CH2:19][N:18]([CH:21]4[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[CH2:25][CH2:26]4)[C:17]3=[O:34])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

Conditions

Temperature: 130 °C

Procedure

A flask was charged with 1H-indazol-5-ol (0.89 g, 0.66 mmol), (R)-tert-butyl 4-(3-(methylsulfonyloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (Preparation D; 0.2 g, 0.55 mmol), K2CO3 (0.092 g, 0.66 mmol), and DMSO (4 mL). The reaction was stirred at 130° C. overnight. Added water and extracted with ethyl acetate. The organic layers were combined, dried, filtered and concentrated. The residue was purified using silica gel column chromatography with 50-100% ethyl acetate in hexanes to provide (S)-tert-butyl 4-(3-(1H-indazol-5-yloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (0.198 g, 90% yield).

Workup

extractionAdded water and extracted with ethyl acetate
customdried
filtrationfiltered
concentrationconcentrated
customThe residue was purified

Sources & evidence

ORD record: ord-7b415ac2b78c4b6b87f6a9cd7b4f4638
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754226B2

Reaction notes

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