Water → HCID 58468062, compound

Participants

Reaction Steps

To a clear solution of 4-[3-(4-Bromo-phenylamino)-propyl]-tetrahydro-pyran-4-carboxylic acid methyl ester (0.74 g, 2.08 mmol) in THF (25 mL) was added a solution of 1.0 mL of potassium t-butoxide (1M in THF) at r.t. (water bath at rt). The clear solution turned a little bit cloudy. After 15 min, TLC (5% MeOH in DCM) showed the reaction is complete (spot to spot), LC/MS detected the product peak. The reaction was cooled tin an ice-water bath, diluted with 25 mL of ethyl acetate, quenched with 10 mL of water. The two layers were separated. The aqueous layer was extracted with EtOAc (2×10 mL). The combined EtOAc extracts were washed with brine, and concentrated on rotavap to yield a crude product as a slightly yellow solid. This material was loaded onto a 25-g of silica gel column, eluted with DCM and 5% MeOH in DCM to get 0.64 g (86% yield) of the title compound as a white solid.

Provenance & Evidence