Water → 2-(5-t-Butylthiophen-2-yl)-cyclopropanecarbonyl-2,6-cis-dimethylmorpholine

HRID 1252467Notes

Reaction equation

[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.[C:9]([C:13]1[S:17][C:16]([CH:18]2[CH2:20][CH:19]2[C:21](Cl)=[O:22])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10].O>[Na]>[C:9]([C:13]1[S:17][C:16]([CH:18]2[CH2:20][CH:19]2[C:21]([N:4]2[CH2:5][C@H:6]([CH3:8])[O:7][C@H:2]([CH3:1])[CH2:3]2)=[O:22])=[CH:15][CH:14]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 20 °C

Procedure

cis-2,6-Dimethylmorpholine (6.6 g, 0.057 mol) was added dropwise to a solution of 2-(5-t-butylthiophen-2-yl)-cyclopropanecarbonyl chloride (2.50 g, 0.01 mol) in sodium dried ether (20 ml) at 10° C. and after complete addition the solution was stirred at 20° C. for 3 hours. The reaction mixture was poured into water and extracted with diethyl ether (2×75 ml). The ethereal extracts were washed with water, dried over anhydrous sodium sulphate, and the solvent removed to give 2-(5-t-butylthiophen-2-yl)-cyclopropanecarbonyl-2,6-cis-dimethylmorpholine as a yellow oil. This oil was separated by column chromatography (silica eluted with petroleum ether/ethyl acetate 1:1) to give 2-(5-t-butylthiophen-2-yl)-trans-cyclopropanecarbonyl)-2,6-cis-dimethylmorpholine (1.70 g, 53%) and 2-(5-t-butylthiophen-2-yl)-cis-cyclopropanecarbonyl)-2,6-cis-dimethylmorpholine (0.94 g, 29%).

Workup

additionafter complete addition the solution
extractionextracted with diethyl ether (2×75 ml)
washThe ethereal extracts were washed with water
dry with materialdried over anhydrous sodium sulphate
customthe solvent removed

Sources & evidence

ORD record: ord-959852de98a34254b3ff354fda6b0c38
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04743602

Reaction notes

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