反应详情

LAH reduction: To a slurry of lithium aluminium hydride (0.72 g) in Et2O (120 ml) was added a solution of (2S,4R)-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid benzyl ester (9.0 g) in Et2O (80 ml) dropwise at −15° C. within 0.5 h. The suspension was stirred for 2 h at the same temperature, then a saturated solution of potassium-sodium tartrate (10 ml) was added dropwise. The slurry was filtered through a pad of filter aid and was washed with Et2O. The combined filtrates were washed with brine, dried over magnesium sulphate and concentrated. The residue was crystallized from acetone/Et2O/hexane to obtain (2S,4R)-[4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-methanol (6.1 g) as a colorless solid, mp 124-125° C.; MS 363 (M).

1. filtrationThe slurry was filtered through a pad of filter aid
2. washwas washed with Et2O
3. washThe combined filtrates were washed with brine
4. dry with materialdried over magnesium sulphate
5. concentrationconcentrated
6. customThe residue was crystallized from acetone/Et2O/hexane