Triethylamine → 2-[(Methanesulfonyl)amino]cyclohexyl 2-methylprop-2-enoate
Reaction equation
[CH3:1][S:2]([NH:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[OH:12])(=[O:4])=[O:3].C(N(CC)CC)C.[C:20](Cl)(=[O:24])[C:21]([CH3:23])=[CH2:22]>C(#N)C>[C:20]([O:12][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]1[NH:5][S:2]([CH3:1])(=[O:4])=[O:3])(=[O:24])[C:21]([CH3:23])=[CH2:22]Participants
Procedure
In a nitrogen atmosphere, a mixture of 108 g of 1,2-epoxycyclohexane, 95.1 g of methanesulfonamide, 11.2 g of t-butoxypotassium, and 1,000 g of tetrahydrofuran was heated under reflux for 100 hours. The reaction solution was neutralized with hydrochloric acid and then subjected to conventional aqueous work-up. Purification by column chromatography yielded an alcohol compound, 2-[(methylsulfonyl)amino]cyclohexanol. In a nitrogen atmosphere, the alcohol compound was combined with 111 g of triethylamine and 2,000 g of acetonitrile, to which 105 g of methacryloyl chloride was added dropwise at −20° C. The mixture was gradually warmed to room temperature and then stirred for 10 hours. The reaction mixture was subjected to conventional aqueous work-up and purified by column chromatography, obtaining 165 g of 2-[(methylsulfonyl)amino]-cyclohexyl methacrylate. The yield was 63% based on the methanesulfonamide.
Workup
- additionwas added dropwise at −20° C
- custompurified by column chromatography
Sources & evidence
- ORD record
- ord-5cb73a06644c4957ba2bc0c31cfdb0fe
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07285368B2
Reaction notes
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