Diisopropylethylamine → (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-hydroxy-3,5-dimethyl-benzylamide

Participants

Reaction Steps

A solution of (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid (67 mg, 0.30 mmol), TBTU (106 mg, 0.33 mmol) and ethyl-diisopropylamine (169 μL, 0.99 mmol) in DMF (2 mL) is allowed to stand at rt for 10 min. A solution of 4-aminomethyl-2,6-dimethyl-phenol (45 mg, 0.30 mmol) in DMF (0.5 mL) is added and the mixture is allowed to stand at rt for 3 h. After the addition of formic acid (0.2 mL) the mixture is separated by HPLC to afford (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-hydroxy-3,5-dimethyl-benzylamide (100 mg) as a colourless oil. LC-MS: tR=1.03 min, [M+1]+=356.23.

Provenance & Evidence