KBS10-3 - Bridge hydrolysis and boc protection of bis-propargyl cyclam about usyd_phd_eln

[KlementineJBS]

11.03.22

• suspended 1.7907 g (2.96 mmol) KBS9 in methanol (35 mL)
• added NaOH (2.5 M, 100 mL)
• left stirring from 9.45 am
• added boc anhydride (1.5499 g, 7.10 mmol, 2.4 equiv) at 11.30 am

[KlementineJBS]

12.03.22

• TLC'd and saw reaction was not complete

• added 1.8044 g (8.27 mmol) propargyl bromide at 5 pm

[KlementineJBS]

15.03.22

• TLC'd at 10 am

• added 555 mg (2.54 mmol, 0.85 equiv.) boc anhydride at 12.45

[KlementineJBS]

16.03.22

• TLC'd again and reaction was not entirely complete. Decided to work up anyway
• removed methanol via rotary evaporation

[KlementineJBS]

18.03.22

• product showed evidence of impurities (overweight, possible water peak on NMR)
• put in dessicator (CaCl2 under vacuum)

[KlementineJBS]

NMR

H NMR (300 MHz, CDCl3): δ 1.45 (s, 18 H), 1.63 (m, 4H), 2.16 (s, 2H), 2.52 (t, 4H), 2.63 (m, 4H), 3.24-3.39 (br m, 12H)

KBS10-3_1.zip

KBS10-3 Processed.pdf

In literature: H NMR (300 MHz, CDCl3): δ 1.45 (s, 18 H), 1.66–1.77 (m, 4 H), 2.17 (s, 2 H), 2.52 (t, J 6.5, 4 H), 2.65 (t, J 6.0, 4 H), 3.25–3.50 (br m, 12 H)

Mass Spec

LRMS

20220419 KBS10-3.d.zip

20220419 KBS10-3.pdf

477.3 [M+H], 499.3 [M+Na]