Iodine → 7-Azabicyclo[4.1.0]heptane, 7-[(4-methylphenyl)sulfonyl]-

HRID 1750227Notes

Reaction equation

[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.II.[CH3:9][C:10]1[CH:11]=[CH:12][C:13]([S:16]([NH:19]Cl)(=[O:18])=[O:17])=[CH:14][CH:15]=1>O1CCOCC1>[C:10]1([CH3:9])[CH:11]=[CH:12][C:13]([S:16]([N:19]2[CH:6]3[CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]3)(=[O:18])=[O:17])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 200 g cyclohexene and 30.7 g iodine in 800 ml of anhydrous dioxane was added 611.7 g of chloramine T. The mixture was stirred at 80° C. for 10 h. After cooling to room temperature the mixture was poured into ice water and extracted with ethyl acetate twice. The combined organic phases were dried over sodium sulphate and concentrated and the residue was purified by chromatography (Silica, hexane/Ethyl acetate) to afford 180 g (29%) of) 7-(Toluene-4-sulfonyl)-7-aza-bicyclo[4.1.0]heptane as a white solid.

Workup

temperatureAfter cooling to room temperature the mixture
extractionextracted with ethyl acetate twice
dry with materialThe combined organic phases were dried over sodium sulphate
concentrationconcentrated
customthe residue was purified by chromatography (Silica, hexane/Ethyl acetate)

Sources & evidence

ORD record: ord-752da06971c14979b82b44e99245685c
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156796B2

Reaction notes

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