Propane-2-sulfonamide → N-[(1S,2R)-2-(4-bromophenoxy)cyclohexyl]propane-2-sulfonamide
Reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]2O)=[CH:4][CH:3]=1.BrC1C=CC(O[C@@H]2CCCC[C@H]2O)=CC=1.[CH3:31][CH:32]([S:34]([NH2:37])(=[O:36])=[O:35])[CH3:33]>>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C@@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]2[NH:37][S:34]([CH:32]([CH3:33])[CH3:31])(=[O:36])=[O:35])=[CH:4][CH:3]=1Participants
Procedure
The title compound of Step 7 was prepared according to the general procedure for the synthesis of cis-N-[2-(4-bromophenoxy)cyclopentyl]propane-2-sulfonamide in Example 5, except that (1S,2R)-2-(4-bromophenoxy)cyclohexanamine was used in place of cis-2-(4-bromophenoxy)cyclopentan-amine, and the product purification was carried out using a gradient of 0% to 1% methanol in dichloromethane. N-[(1S,2R)-2-(4-bromophenoxy)cyclohexyl]propane-2-sulfonamide was obtained as a white foam. Yield: 1.67 g, 4.44 mmol, 75%. 1H NMR (400 MHz, CDCl3) δ 1.36 (d, J=6.9 Hz, 3H), 1.37 (d, J=6.9 Hz, 3H), 1.37-1.48 (m, 4H), 1.77-1.88 (m, 3H), 2.06 (m, 1H), 3.12 (septet, J=6.8 Hz, 1H), 3.54 (m, 1H), 4.48 (d, J=9.5 Hz, 1H), 4.54 (m, 1H), 6.84 (d, J=9.0 Hz, 2H), 7.39 (d, J=9.0 Hz, 2H). The enantiomer of N-[(1S,2R)-2-(4-bromophenoxy)cyclohexyl]propane-2-sulfonamide was prepared using similar chemistry to that described above in this Step 7, but employing (1S,2S)-2-(4-bromophenoxy)cyclohexanol as starting material instead of (1R,2R)-2-(4-bromophenoxy)cyclohexanol. The absolute stereochemistry of the enantiomer of N-(1S,2R)-2-(4-bromophenoxy)cyclohexyl]propane-2-sulfonamide was established via X-ray crystallography.
Sources & evidence
- ORD record
- ord-2750bcb051994e69b9148de2867b6d38
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278457B2
Reaction notes
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