Methyl p-toluenesulfonate → 3-Pyrrolidinol, 1-[(4-methylphenyl)sulfonyl]-, 3-(4-methylbenzenesulfonate), (3S)-

Participants

Reaction Conditions

Reaction Steps

Methyl para-toluenesulphonate (54 g) was added in portions to a solution of 1-tosyl-3-(R)-(-)-hydroxypyrrolidine (49 g-see Preparation 2) and triphenylphosphine (76 g) in anhydrous tetrahydrofuran (700 ml) at 0° C. The mixture was cooled to -20° C. and diethyl azodicarboxylate (58 g-"DEAD") was added, dropwise, over 30 minutes. During this time, the temperature of the mixture was not allowed to rise above -10° C. When the addition was complete the mixture was allowed to warm to room temperature and stirred for 16 hours. The mixture was concentrated in vacuo to give a solid which was purified by column chromatography on silica eluting with hexane containing dichloromethane (50%). The product-containing fractions were combined and concentrated in vacuo to give an oil which was crystallised from 1-propanol to give the title compound as a colourless solid, yield 56 g, m.p. 110° C., [α]D25 -5.2°(c 1.0, CH2Cl2).

Provenance & Evidence