Iodine → cis Ethyl 3-bromo-2-oxo-1-azacyclodecane-10-carboxylate

HRID 5391

Reaction equation

[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:3]1.P(Cl)(Cl)(Cl)(Cl)Cl.II.[Br:25]Br>C(Cl)Cl>[Br:25][C@H:11]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:3][C:2]1=[O:1]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl 2-oxo-1-azacyclodecane-10-carboxylate (4.0 g, 17.6 mmol) is dissolved in methylene chloride (50 mL), and cooled to 0° C. Phosphorus pentachloride (3.85 g, 18.5 mmol) and iodine (0.051 g, 0.2 mmol) are added. The reaction is stirred for 15 minutes at 0° C. Then, bromine (3.10 g, 19.4 mmol) is added, and the reaction is stirred at 0° C. for 4 hours. The reaction is quenched by adding saturated sodium sulfite (until the color of excess bromine disappears), and extracted several times with methylene chloride. The combined organic layers are dried (Na2SO4), and the solvent is evaporated. The product is purified by silica gel chromatography (15% ethyl acetate/hexane) to give cis ethyl 3-bromo-2-oxo-1-azacyclodecane-10-carboxylate, m.p. 132°-134° C.

Workup

stirringthe reaction is stirred at 0° C. for 4 hours
customThe reaction is quenched
additionby adding saturated sodium sulfite (until the color of excess bromine
extractionextracted several times with methylene chloride
dry with materialThe combined organic layers are dried (Na2SO4)
customthe solvent is evaporated
customThe product is purified by silica gel chromatography (15% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-506b9adb631a461cb9ffccba8d2f7bb0
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05244889

Linked notes

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