1-N,1-N,3-trimethylbutane-1,3-diamine

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

Procedure: Solid CbzOSu (15.6 g, 1 equiv, 48.8 mmol) was added in one portion to a solution of N1,N1-3-trimethylbutane-1,3-diamine (8.15 g, 62.6 mmol) in THF (100 mL). The reaction was left to stir at room temperature for 17 h. The solvent was removed and the residue was taken up in a mixture of ethyl acetate (500 mL) and water (100 mL). The layers were separated and the organic layer washed with saturated sodium bicarbonate (2×100 mL), water (100 mL) and brine (100 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated to a pale yellow oil. The crude oil was purified on an ISCO purification system with gradient elution from 1-5% methanol in DCM. The desired fractions were collected and concentrated to give a colorless oil (11.49 g, yield: 69.6%). 1H NMR (CDCl3, 400 MHz): δ 1.35 (s, 6H), 1.67-1.72 (t, J=6.6, 2H), 2.23 (s, 6H), 2.36-2.40 (t, J=7.2, 2H), 6.46 (s, 1H), 7.27-7.36 (m, 5H), LRMS (ESI+) for C15H24N2O2 (264.2); Found: 265 (MH+). The reaction was left The solvent was removed the residue was taken up in a mixture of ethyl acetate (500 mL) and water (100 mL) The layers were separated the organic layer washed with saturated sodium bicarbonate (2×100 mL), water (100 mL) and brine (100 mL) The organic layer was dried over anhydrous MgSO4 filtered concentrated to a pale yellow oil The crude oil was purified on an ISCO purification system with gradient elution from 1-5% methanol in DCM The desired fractions were collected concentrated

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

Procedure: N-(Benzyloxycarbonyloxy)succinimide (15.6 g, 1 equiv, 62.6 mmol) was added in one portion to a solution of N1,N1-3-trimethylbutane-1,3-diamine (8.15 g, 62.6 mmol) in tetrahydrofuran (100 mL). The reaction was left to stir at room temperature for 17 hours. The solvent was removed and the residue was taken up in a mixture of ethyl acetate (500 mL) and water (100 mL). The layers were separated and the organic layer washed with saturated sodium bicarbonate (2×100 mL), water (100 mL) and brine (100 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated to a pale yellow oil. The crude oil was purified by flash chromatography (1% to 5% methanol in dichloromethane). The desired fractions were collected and concentrated to give a colorless oil (11.49 g, yield: 69.6%)1H NMR (CDCl3, 400 MHz): δ 1.35 (s, 6H), 1.67-1.72 (t, J=6.6, 2H), 2.23 (s, 6H), 2.36-2.40 (t, J=7.2, 2H), 6.46 (s, 1H), 7.27-7.36 (m, 5H); LRMS (ESI/APCI) m/z 265 [M+H]+. The reaction was left The solvent was removed the residue was taken up in a mixture of ethyl acetate (500 mL) and water (100 mL) The layers were separated the organic layer washed with saturated sodium bicarbonate (2×100 mL), water (100 mL) and brine (100 mL) The organic layer was dried over anhydrous MgSO4 filtered concentrated to a pale yellow oil The crude oil was purified by flash chromatography (1% to 5% methanol in dichloromethane) The desired fractions were collected concentrated