2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4 (50 mg, 0.27 mmol) in CH2Cl2 (3 mL) was added sat. NaHCO3 (3 mL). Under stirring, bromoacetyl bromide (80 mg, 040 mmol) was added. The pH was controlled in the range 8-9 by adding solid NaHCO3. The reaction was stirred at rt for 15 min. CH2Cl2 (5 mL) was added and the reaction mixture was extracted 5×3 mL CH2Cl2. The organic layers were combined, washed with brine, dried with Na2SO4. The solvent was evaporated and the residue was purified by FCC to afford 5 as clear oil (65 mg, 78%). 1H NMR (400 MHz, CDCl3): δ 2.42 (t, J=2.4 Hz, 1H), 3.48 (dd, J=5.2, 5.2 Hz, 2H) 3.57 (t, J=5.2 Hz, 2H), 3.62 (m, 4H), 3.66-3.70 (m, 4H), 3.85 (s, 2H), 4.18 (d, J=2.4 Hz, 2H). 6.91 (bs, 1H). 13C NMR (100 MHz, CDCl3): δ 29.35, 40.11, 58.65, 69.32, 69.56, 70.53, 70.61, 70.76, 74.90, 79.73, 165.86. ESIMS calcd for C11H18BrNNaO4 [M+Na]+ 330.03, 332.03, found: 330.33, 332.46. The reaction was stirred at rt for 15 min the reaction mixture was extracted 5×3 mL CH2Cl2 washed with brine dried with Na2SO4 The solvent was evaporated the residue was purified by FCC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: in a 50 mL flask, 3 (150 mg, 0.7 mmol), Ph3P were dissolved in 10 mL THF. The reaction mixture was stirred at rt for 3 hr. To the reaction mixture was added H2O (1 mL) the resultant mixture was stirred for 36 hr at rt. The solvent was evaporated and the residue was purified by FCC to afford 4 as slightly yellow oil (131 mg, quant.). 1H NMR (400 MHz, CDCl3): δ 1.46 (br, 2H), 2.35 (t, J=1.6 Hz, 1H), 2.73 (t, J=5.2 Hz, 2H), 3.38 (t, J=5.2 Hz, 2H) 3.50-3.59 (m, 10H), 4.08 (m, 2H). 13C NMR (100 MHz, CDCl3): δ 41.72, 58.34, 69.04, 70.21, 70.36, 70.54, 73.36, 74.63, 79.60. ESIMS calcd for C9H18NO3 [M+H]+ 188.13, found: 188.16. FTIR (NaCl plate, CH2Cl2): 1118 (C—O str), 2111 (C≡C str), 2869 (C—H str), 3249 (N—H str). was stirred for 36 hr at rt The solvent was evaporated the residue was purified by FCC to afford 4 as slightly yellow oil (131 mg, quant.)