KBS19-1 - Deprotection of bis-methylferrocenylcyclam about usyd_phd_eln

[KlementineJBS]

18.07.22

1. Dissolved KBS18 (138 mg, 0.144 mmol) in ~ 1 mL dioxane (in vial) and added 1 drop water.
2. Added 1.0 mL HCl (4 M in dioxane)
3. Sonicated for 5 minutes upon which the amber coloured liquid turned to a mustard yellow precipitate

4. Stirred for a further 30 minutes
5. TLC indicated completion

6. Rotovapped off excess liquid

Vial (empty): 15.9518 g
Vial (full): 16.0886 g
Mass: 136.8 mg

[KlementineJBS]

19.07.22

Decided to convert some product to the free base using Ambersep 900 hydroxide form.

1. Pre-rinsed one spatulaful of Ambersep beads (3 x with methanol)
2. Added ~ 8 mL MeOH and allowed to swell for 15 minutes
3. Added KBS19-1 (63 mg, 0.0758 mmol) dissolved in MeOH (10 mL) by solution transfer with rinsing - took ~ 20 minutes to get it all in due to solubility issues
4. Allowed to stir for 25 minutes
5. Filtered (Buchner funnel) and rotovapped down

Vial (empty) = 15.9779 g
Vial (full) = 16.0347 g
Mass = 56.8 mg

[KlementineJBS]

20.07.22

LRMS

20220720_KBS19-1.d.zip
KBS19-1.pdf

Column

Empty vial: 15.6242 g
Full vial: 15.6662 g
Mass: 42 mg

[KlementineJBS]

06.09.22

IR

KBS19-1.zip

KBS19-1.pdf

[KlementineJBS]

07.09.22

Vial with crude product: 16.3609

[KlementineJBS]

26.09.22

19-1 FB

Only a tiny amount left - if empty vial is indeed 15.9779 g, then remaining mass is just 13.8 mg.

Left on hi vac overnight.

19-1 HCl salt

Added NMR tube contents to vial (H2O/MeOH). Empty vial weight is apparently 15.9518.

[KlementineJBS]

10.11.22

Found additional amount of 19-1 FB (in an NMR tube; not triturated so not as clean).

KBS19-1 FB 10-11-22_1.zip

Will clean and use for final characterisation.