Methanesulfonyl chloride → HCID 57420362, compound
Reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].[BH4-].[Na+].[CH3:10][S:11](Cl)(=[O:13])=[O:12]>>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][O:7][S:11]([CH3:10])(=[O:13])=[O:12]Participants
Procedure
Amine preparation: 2-Thiazolecarboxaldehyde was converted to the corresponding alcohol by treatment with sodium borohydride. Reaction with methanesulfonyl chloride yielded methanesulfonic acid thiazol-2-ylmethyl ester. A mixture of methanesulfonic acid thiazol-2-ylmethyl ester (393 mg), (3R,5S)-3,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (described previously, 435 mg), potassium carbonate (309 mg) and tetrabutyl ammonium iodide (827 mg) was heated to reflux in MeCN (10 mL). After 4 days the reaction mixture was cooled, diluted with ethyl acetate, washed with water and dried (MgSO4). The solvent was evaporated and the residue purified by flash chromatography to give (R)-3,5-dimethyl-4-thiazol-2-ylmethyl-piperazine-1-carboxylic acid (S)-tert-butyl ester (314 mg). Treatment of this compound with HCl in DCM/MeOH yielded the desired amine, which was isolated as the hydrochloride salt.
Sources & evidence
- ORD record
- ord-f17fd10d4ef849e99f6947ec7c592add
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07750002B2
Reaction notes
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