Lithium Hydroxide → (2S)-1-(Benzenesulfonyl)pyrrolidine-2-carboxylic acid

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Reaction Steps

To a solution of 38.2 g (0.142 mol) of the above methyl ester 7 in 500 mL methanol was added 140 mL (0.28 mol) of freshly-prepared 2 M aqueous LiOH with stirring to give a colorless solution. This was stirred overnight, after which HPLC showed no starting material. The solution was reduced by 50% in vacuo and partitioned between 1 N HCl and CH2Cl2 (˜200 mL each). The phases were separated and the aqueous layer was washed again with CH2Cl2. The organic phases were combined, dried (MgSO4), and concentrated to a white solid. This was recrystallized twice from ethyl acetate/hexanes to give 34.7 g (0.136 mol, 96%) of 8 as fine white needles. M/z=256.2 (M+H+).

Provenance & Evidence