Triethylamine → HCID 58619009, compound

Participants

Reaction Steps

tert-Butyl 4-[(1S)-1-azido-2-oxo-2-(1,3-thiazolidin-3-yl)ethyl]piperidine-1-carboxylate (Example 96, step B, 215 mg, 0.6 mmol) was dissolved in a freshly prepared HCl in methanol (1 mL acetyl chloride in 9 mL of methanol) and stirred for 4 h and concentrated to remove the Boc group. A portion of this material (29 mg, 0.1 mmol) was dissolved in methylene chloride (1 mL) and triethylamine (0.041 mL, 0.3 mmol) and 4-iodobenzylbromide (44 mg, 0.15 mmol) was added. The reaction mixture was stirred for 8 h, concentrated and purified by flash chromatography (silica gel, eluent: 20% acetone in CH2Cl2) to give the 4-iodobenzylamine. This material was dissolved in wet THF (10% water) and triphenyl phosphine (26 mg, 0.1 mmol) was added. The reaction mixture was heated in an oil bath at 60° C. for 3 h, concentrated and subjected to preparative TLC on silica gel (eluent: 10% MeOH in CH2Cl2) to afford 32 mg of the title compound. 1H NMR (500 MHz, CD3OD) δ 7.85 (d, 2H, J=6 Hz), 7.34 (d, 2H, J=6 Hz), 4.75–4.46 (m, 2H), 4.38–4.28 (m, 1H), 4.47 (s, 2H), 3.92–3.64 (m, 2H), 4.53 (bs, 2H), 3.16–3.02 (m, 4H), 2.19 (m, 1H), 1.98 (m, 2H), 1.83 (m, 2H).

Provenance & Evidence