Tetrabutylammonium Fluoride → HCID 86669236, compound

Participants

Reaction Steps

To a solution of 1-methylethyl {(2S,4R)-1-acetyl-2-methyl-6-[(trimethylsilyl)ethynyl]-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (for a preparation, see Intermediate 59) (216 mg, 0.559 mmol) in tetrahydrofuran (THF) (3 mL) at room temperature was added TBAF (1M in THF, 0.671 mL, 0.671 mmol) and the resulting black mixture was stirred at this temperature for 35 min. Most of the solvent was removed in vacuo and the residue dissolved in AcOEt. The organic phase was washed with a saturated NaHCO3 aqueous solution then twice with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue on SP4 using a 10 G silica cartridge (Gradient: 13 to 63% AcOEt in Hexanes) gave 1-methylethyl[(2S,4R)-1-acetyl-6-ethynyl-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (156 mg, 0.496 mmol, 89% yield) as a very pale yellow foam.

Provenance & Evidence