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KlementineJBS / USYD_PhD_ELN

This repository forms the electronic laboratory notebook (ELN)for Klementine Burrell-Sander's PhD's
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KBS19-1 - Deprotection of bis-methylferrocenylcyclam #21

Closed KlementineJBS closed 1 year ago

KlementineJBS commented 2 years ago

Link to HIRAC, original method and [master page.

KBS19 Deprotection of bis-methylferrocene cyclam.docx

Reaction scheme

KBS19 Bis-methylferrocene cyclam deprotection

Outcome

137 mg - impure

KlementineJBS commented 2 years ago

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
  1. Stirred for a further 30 minutes
  2. TLC indicated completion
  1. Rotovapped off excess liquid

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

KlementineJBS commented 2 years ago

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 commented 2 years ago

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 commented 2 years ago

06.09.22

IR

KBS19-1.zip

KBS19-1.pdf

KlementineJBS commented 2 years ago

07.09.22

Vial with crude product: 16.3609

KlementineJBS commented 2 years ago

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 commented 1 year ago

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.