Borane → HCID 178502739, compound

Participants

Reaction Steps

To an ice cold solution of 3.0 g of cis-[3-(methoxy-methyl-carbamoyl)-cyclobutyl]-acetic acid in 50 mL of THF was added 15 mL of 1M borane in THF. The mixture was allowed to stir for 15 min in the cold, then warm and stir for 30 min. The reaction was quenched with 25 mL of 10% HCl and extracted into 3×50 mL of ethyl acetate. The combined extracts were diluted with 50 mL of toluene, dried over magnesium sulfate and concentrated under reduced pressure. Drying under vacuum overnight gave 1.8 g of product as a colorless oil: MS (m+1)=188.45; 1H NMR (400 MHz, CDCl3) 3.62 (s, 3H), 3.6 (t, 2H), 3.18 (s, 3H), 2.35 (m, 1H), 2.3 (m, 3H), 1.984 (dd, 2H), 1.65 (dd, 2H).

Provenance & Evidence