(S)-2-((R)-2-methyl-pentyl)-succinic acid 4-tert-butyl ester → (3S,5R)-3-Hydroxymethyl-5-methyl-octanoic Acid Tert-butyl Ester

Participants

Reaction Steps

To acid 102 (3.68 g, 0.014 mol) in THF (100 mL) at 0° C. was added BH3.Me2 (36 mL of a 2 M solution in THF, Aldrich) upon which the solution was warmed to room temperature. After 15 hours ice was carefully added (in order to control the effervescence) to the solution followed by brine. The solution was extracted with ether and the combined organic phases dried (MgSO4) and concentrated under reduced pressure. Flash chromatography (4:1 hexane/EtOAc) gave alcohol 103 as an oil (2.0 g, 59%). 13C NMR (100 MHz; CDCl3) 173.56, 80.85, 65.91, 39.74, 39.20, 38.90, 35.65, 29.99, 28.31, 20.18, 19.99, 14.56.

Provenance & Evidence