p-Toluenesulfonic acid monohydrate → HCID 86599621, compound
Reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]#[N:15])=O)(C)(C)C.O.[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([OH:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1>C(#N)C>[OH:13][C@H:11]1[CH2:12][NH:8][C@H:9]([C:14]#[N:15])[CH2:10]1.[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([O-:27])(=[O:26])=[O:25])=[CH:22][CH:23]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
6.40 g (30 mmol) of (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxy-pyrrolidine-2-carbonitrile was dissolved in 100 ml of acetonitrile and 8.56 g (45 mmol) of 4-methylbenzenesulphonic acid monohydrate was added to the solution. The mixture was stirred at room temperature for 24 hours and was evaporated under reduced pressure. 500 ml of diethyl ether was added to the resulting brown oil. It was stirred 10 minutes and kept in the refrigerator for a night. The resulting white crystalline material was filtered off and washed with diethyl ether. 6.31 g (73%) of the above product are obtained. M.p.: 110-113° C.