Diisopropylethylamine → HCID 11618538, compound

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 (9.6 mg, 0.043 mmol), TBTU (13.8 mg, 0.043 mmol) and ethyl-diisopropylamine (22 μL, 0.129 mmol) in DMF (1 mL) is allowed to stand at rt for 30 min. The solution is added to (rac)-1-(4-aminomethyl-3-methoxy-phenoxy)-propan-2-ol (9.1 mg, 0.043 mmol) and the mixture is allowed to stand at rt for 1 h. The mixture is separated by prep. HPLC to afford (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((R/S)-2-hydroxy-propoxy)-2-methoxy-benzylamide (7.6 mg) as a colourless oil. LC-MS: tR=0.98 min, [M+1]+=402.16; 1H NMR (CDCl3): δ 7.20 (d, J=8.2 Hz, 1H), 6.50 (d, J=2.3 Hz, 1H), 6.44 (d, J=8.2 Hz, 1H), 6.16 (t br, J=5.3 Hz, 1H), 4.47 (d, J=5.9 Hz, 2H), 3.93 (dd, J=2.9, 11.1 Hz, 1H), 3.87 (s, 3H), 3.82-3.72 (m, 1H), 2.90 (dd, J=5.3, 17.6 Hz, 1H), 2.69 (d, J=18.1 Hz, 1H), 2.35 (s, 3H), 1.92-1.85 (m, 2H), 1.30 (d, J=6.4 Hz, 3H), 1.11 (s, 3H), 0.72 (s, 3H).

Provenance & Evidence