Lithium borohydride → 3-(tert-Butyldimethylsilanyloxy)-2-hydroxymethylpyrrolidine-1-carboxylic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

A solution containing 39 (12 g, 33 mmol) in THF (50 mL) was cooled to 0° C. LiBH4 in THF (2M, 20 mL) was added in a dropwise fashion. After 1 h, the solution was warmed to ambient temperature. After 2 h, the solution was diluted with MeOH, then 120, and concentrated. The residue was extracted with EtOAc, washed with 1M HCl, saturated aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 9.5 g (87%) of 40 as a colorless oil.3 3Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry, 1994, 5, 119.

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