Iodine → HCID 57211612, compound

HRID 466778Notes

Reaction equation

[CH2:1]([C@:8]1([CH3:22])[C:13]([O:14][CH2:15][CH3:16])=[N:12][C@@H:11]([CH:17]([CH3:19])[CH3:18])[C:10]([O:20]C)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.II.C[Si](I)(C)C.C(NCC)C>ClCCl.C(O)C>[CH2:1]([C@:8]1([CH3:22])[C:13]([O:14][CH2:15][CH3:16])=[N:12][C@@H:11]([CH:17]([CH3:18])[CH3:19])[C:10](=[O:20])[NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -10 °C

Procedure

0.3 g of (2R,5S)-2-benzyl-2,5-dihydro-3-ethoxy-5-isopropyl-6-methoxy-2-methylpyrazine was dissolved in 15 ml of absolute dichloromethane and cooled under argon to -10° C. Then 25 mg of iodine and 0.16 ml of trimethylsilyl iodide were added. After 3 h, the solution was allowed to warm to room temperature and was stirred at 22° C. for 14 h. 5 ml of ethanol and 5 ml of diethylamine were added and the mixture was then evaporated under reduced pressure and the residue was chromatographed on silica gel (ether, Rf=0.44). 0.29 g (91%) of (2R,5S)-2-benzyl-3-ethoxy-5-isopropyl-1,2,5,6-tetrahydro-2-methyl-6-pyrazinone, melting point 125° C., was obtained.

Workup

temperatureto warm to room temperature
customthe mixture was then evaporated under reduced pressure
customthe residue was chromatographed on silica gel (ether, Rf=0.44)

Sources & evidence

ORD record: ord-c163347669804a87ad44be743e89055e
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05157145

Reaction notes

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