Water → HCID 18458648, compound

HRID 2304809Notes

Reaction equation

[OH:1][CH:2]1[C:7]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][C:11]([O:16][CH3:17])=[CH:10][C:9]=2[O:18][CH3:19])=[CH:6][CH2:5][N:4]([CH3:20])[CH2:3]1.C(N(CC)CC)C.Cl[C:29]([O:31][CH3:32])=[O:30].O>O1CCCC1>[CH3:32][O:31][C:29]([O:1][CH:2]1[C:7]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][C:11]([O:16][CH3:17])=[CH:10][C:9]=2[O:18][CH3:19])=[CH:6][CH2:5][N:4]([CH3:20])[CH2:3]1)=[O:30]

Participants

Conditions

Temperature: 5 °C

Procedure

8.37 g (30 mmol) of 3(R,S)-hydroxy-1-methyl-4(2,4,6-trimethoxyphenyl)-1,2,3,6-tetrahydropyridine (VII) were dissolved in 83.7 ml of tetrahydrofuran and treated with 12.4 ml (90 mmol) of triethylamine. The mixture was cooled to 5° C., 2.55 ml (33 mmol) of methyl chloroformate were added dropwise in the course of 15 min and the mixture was stirred at 5-10° C. for a further 3 h. Since TLC checking still showed starting material, a further 1.0 ml (12.9 mmol) of methyl chloroformate were added and the mixture was stirred again for 1 h. 50 ml of water were then added and the mixture was extracted twice with 50 ml of ethyl acetate each time. The combined organic phases were washed with 30 ml of saturated sodium chloride solution, then dried over sodium sulfate and evaporated in vacuo on a rotary evaporator.

Workup

stirringthe mixture was stirred again for 1 h
extractionthe mixture was extracted twice with 50 ml of ethyl acetate each time
washThe combined organic phases were washed with 30 ml of saturated sodium chloride solution
dry with materialdried over sodium sulfate
customevaporated in vacuo on a rotary evaporator

Sources & evidence

ORD record: ord-9ed9221d87ce4736862da8248bd91d4d
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06437136B1

Reaction notes

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