Ammonia → HCID 21350207, compound

HRID 1359372Notes

Reaction equation

[CH2:1]([C:8]1[C:13]([O:14][CH2:15][O:16][CH3:17])=[CH:12][CH:11]=[C:10](I)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:19][C@H:20]1[CH2:24][CH2:23][NH:22][C:21]1=[O:25].C(=O)([O-])[O-].[K+].[K+].N>CN1CCCC1=O.C(OCC)(=O)C>[CH2:1]([C:8]1[C:13]([O:14][CH2:15][O:16][CH3:17])=[CH:12][CH:11]=[C:10]([N:22]2[CH2:23][CH2:24][C@H:20]([OH:19])[C:21]2=[O:25])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

14.3 g of 2-benzyl-3-methoxymethyloxy-6-iodopyridine (Production Example 12) and 4.1 g of (3S)-3-hydroxy-2-pyrrolidinone synthesized according to a method well-known in a literature (Synthesis, 1978, 614), 4.6 g of cuprous iodide and 13.7 g of potassium carbonate were suspended in 30 ml of 1-methyl-2-pyrrolidinone, followed by heating under stirring at 140° C. in an oil bath for 20 minutes in a nitrogen atmosphere. After cooling as it was, ethyl acetate and aqueous ammonia were added thereto. The mixture was extracted with ethyl acetate, and the organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 50-60% ethyl acetate as an eluent for separation and purification, to give 9.7 g of the target compound.

Workup

temperatureby heating
temperatureAfter cooling as it
extractionThe mixture was extracted with ethyl acetate
washthe organic phase was further washed with brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was removed
customfor separation and purification

Sources & evidence

ORD record: ord-7c60aca5584342ae921c235c1a77c595
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599917B1

Reaction notes

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