Acetic Acid → HCID 68951075, compound

Participants

Reaction Steps

To a solution (4-bromo-phenyl)-pyrrolidin-3-yl-methanone (2.24 g, 8.81 mmol) in methanol (44 mL), add acetic acid (1.01 mL, 17.6 mmol) and formaldehyde (2.15 g, 26.4 mmol, 37% aqueous solution). After 15 min, add sodium triacetoxyborohydride (5.60 g, 26.4 mmol) and allow the mixture to stir at RT for one hour. Concentrate the reaction mixture. Add water and adjust the solution to pH=10 with 2 N NaOH. Extract the aqueous with ethylacetate. Dry the combined organic layers over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatography, eluting with 5-10% MeOH (2N NH3)/CH2Cl2 to give 1.61 g (68%) of the title compound. LC-MS/ES m/z (79Br) 268.0 [M+H]+.

Provenance & Evidence