KBS3: Boc protection of 1,6 diaminohexane
(From an attempt not included on GitHub)
Di-tert-butyl dicarbonate (3.6 mL, 15.66 mmol) in chloroform (12 mL) was added dropwise to a solution of 1,6-diaminohexane (745 mg, 6.41 mmol) in chloroform (18 mL). The mixture was left to stir for 25 hours at room temperature before being concentrated at reduced pressure. The residue was diluted with water (40 mL) and extracted with chloroform (3 x 40 mL). The combined organic extracts were washed with aqueous NaHCO3 (40 mL) and with brine (40 mL), then dried over MgSO¬4. After being concentrated under reduced pressure, the compound was purified by flash column chromatography (EtOAc:hexane = 1:4) to yield a white crystalline powder (1.44 g, 71%).
1H NMR (300 MHz, CDCl3) δ 4.54 (s, 2H), 3.12 (q, J = 6.7 Hz, 4H), 1.46 (s, 20 H), 1.35 (q, J = 4.2, 3.8 Hz, 4H).
LRMS (ESI+) m/z 339.2 [M + Na]+, 655.4 [2M + Na]+.
lit. = 102 - 104 C (in solution) or 101 - 103 C
experimental = 102 - 105 C
Earlier attempts are not on GitHub.
KBS3-3 - 115%
Nil so far.