Water → HCID 66961828, compound

HRID 2406776Notes

Reaction equation

CS([O:5][CH2:6][C@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=O)=O.O[C:20]1[C:21]([C:26]#[N:27])=[N:22][CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:26]([C:21]1[C:20]([O:5][CH2:6][C@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:25][CH:24]=[CH:23][N:22]=1)#[N:27]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of tert-butyl (2R)-2-[(methanesulfonyloxy)methyl]pyrrolidine-1-carboxylate (7.38 g, 26.4 mmol, Tetrahedron Asymmetry, 1997, 8, 2209-2213), 3-hydroxypicolinonitrile (4.76 g, 39.6 mmol), and potassium carbonate (10.95 g, 79.0 mmol) in N,N-dimethylformamide (150 mL) was stirred at 100° C. for 6 h. After cooling to room temperature, the mixture was poured into water, and the aqueous layer was extracted with ethyl acetate twice. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residual oil was purified by silica gel column chromatography (ethyl acetate/hexane 1:2 to 1:1) to give 3.62 g (45%) of the title compound as a colorless oil.

Workup

temperatureAfter cooling to room temperature
extractionthe aqueous layer was extracted with ethyl acetate twice
dry with materialThe combined organic layers were dried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residual oil was purified by silica gel column chromatography (ethyl acetate/hexane 1:2 to 1:1)

Sources & evidence

ORD record: ord-eaedd0474ec7444ebbfc15e88439b3a4
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809380B2

Reaction notes

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