Tetrabutylammonium Fluoride → HCID 66849549, compound

Participants

Reaction Steps

3-[3-(tert-Butyl-dimethyl-silanoxy)-1-(S)-methyl-propylamino]-5-(3,3-dimethyl-but-1-ynyl)thiophene-2-carboxylic acid methyl ester (8.2 g, 18.24 mmol) was taken up in THF (200 mL). TBAF 1.0M in THF (88.15 mL, 88.15 mmol) was added in 20 mL increments at rt. The reaction was monitored by LC/MS. The reaction was determined to be complete at 30 min. and was quenched with sat NH4Cl(aq) (200 mL). After stirring at it for 1 h. the organics were removed under reduced pressure and treated with EtOAc. The solution was dried over Na2SO4, solids were filtered and the solvent removed under reduced pressure. 5-(3,3-dimethyl-but-1-ynyl)3-(3-hydroxy-1-(S)-methyl-propylamino)-thiophene-2-carboxylic acid methyl ester (4.0 g, 73%) was isolated by silica gel chromatography as a yellow solid.

Provenance & Evidence