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KBS3: Boc protection of 1,6 diaminohexane

Klementine Burrell-Sander edited this page May 2, 2023 · 1 revision

Method

(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%).

Characterisation

NMR

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).

Mass spec

LRMS (ESI+) m/z 339.2 [M + Na]+, 655.4 [2M + Na]+.

Melting Point

lit. = 102 - 104 C (in solution) or 101 - 103 C

experimental = 102 - 105 C

Attempts

Honours

Earlier attempts are not on GitHub.

KBS3-3 - 115%

PhD

Nil so far.

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