2-Methoxyethylamine → HCID 67311514, compound

Participants

Reaction Steps

Wang resin (1.11 mmol/g, 1.00 g) in a polypropylene filtration tube with a polyethylene frit was added DMF (5 mL) and CH2Cl2 (5 mL), followed by 4-formylcinnamic acid (5.5 mmol, 969 mg), DMAP (1.08 mmol, 132 mg) and diisopropylcarbodiimide (5.5 mmol, 861 μL). The mixture was shaken at room temperature for 24 hours. The resulting resin was washed with DMF (3×5 mL), MeOH (3×5 mL) and CH2Cl2 (4×5 mL), then dried in vacuo. To the resin (100 mg) was added 2-methoxyethylamine (1.1 mmol, 96 μL) in DMF (1 mL), Na(OAc)3BH (2.2 mmol, 466 mg) and acetic acid (25 μL). After shaking at room temperature overnight, the resulting resin was washed with DMF (3×1 mL), MeOH (3×1 mL) and CH2Cl2 (4×1 mL), then dried in vacuo. The resulting resin was suspended in a solution of trans-cinnamaldehyde (1.1 mmol, 139 μL), Na(OAc)3BH (2.2 mmol, 466 mg) and acetic acid (10 μL) in DMF (1 mL). The mixture was shaken at room temperature for 24 hours. The resulting resin was washed with DMF (3×1 mL), MeOH (3×1 mL) and CH2Cl2 (4×1 mL), then dried in vacuo. To the dry resin was added polyamine resin and CH2Cl2. The mixture was agitated at room temperature for 24 hours, then filtered and washed with CH2Cl2 (2×1.5 mL). The filtrates were collected and evaporated to yield 21 as a colorless oil (LRMS m/z 351).

Provenance & Evidence