Potassium Bromide → (1S,2R)-4'-(4-Chlorophenyl)-2',3',9'-trimethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of ((1S,2R)-4′-(4-chlorophenyl)-2′,3′,9′-trimethylspiro[cyclopropane-1,6′-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]-2-yl)methanol (300 mg, 0.752 mmol) in DCM (5 mL), a solution of 4-methoxy TEMPO (0.0135M in DCM) (1 mL, 0.0135 mmol), a solution of Aliquat 336 (0.074M in DCM) (0.5 mL, 0.037 mmol) and a solution of potassium bromide (0.25M in water) (0.3 mL, 0.075 mmol) were mixed and cooled to 0° C. before a solution of sodium hypochlorite (0.35M in water; buffered with NaHCO3 to pH˜8.6) was slowly added. After 30 min of vigorous stirring at 0° C., the aqueous layer was extracted with DCM. 2-Methyl-2-butene (0.5 mL) was added to the organic layer, before it was concentrated to dryness. The residue was used in the next step without purification. LRMS (M+H)+: 397 m/z.

Provenance & Evidence