KlementineJBS / USYD_PhD_ELN

This repository forms the electronic laboratory notebook (ELN)for Klementine Burrell-Sander's PhD's

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KBS30-5 - N-alkylation with KBS29 #169

Closed KlementineJBS closed 5 months ago

KlementineJBS commented 9 months ago

Link to HIRAC and master page.

Previous attempt is #165

KBS30 - Generic alkylation of 1,x-diaminoalkane with naphthalene-triazole pendant (updated).docx

Notes

Using sodium hydride as base instead of potassium carbonate.

Reaction scheme

KBS30 alternative nosyl protected

Outcome

Bis product: 14.1 mg, 0.0157 mmol, 10% Mono product: 4.6 mg, 0.0066 mol, 4% Mixed: 13.9 mg (max. 12%)

KlementineJBS commented 9 months ago

12.12.23

Added linear amine SM (78.1 mg, 0.161 mmol) to a flask with NaH (14 mg, 0.348 mmol, 2.2 equiv., 60% mineral oil dispersion) and dissolved in dry DMF (2 mL)
Backfilled and evacuated x 5
Left stirring for ~30 minutes
Put on ice and added pendant group KBS29 (100 mg, 0.348 mmol, 2.2 equiv.) dissovled in dry DMF (2 mL). Left stirring from ~ 2.15 pm

TLC consistently indicated that pendant SM was not consumed. A new spot, closer to the baseline than the linear amine SM, formed - it is unknown what this is. Potentially hydrolysis of the KBS29 pendant again.

Reaction was heated to 50 C for ~ 2hrs but this had little effect. Reaction turned off at 5.30 pm.

KlementineJBS commented 9 months ago

14.12.23

Reaction had been left untended due to power outages. Quenched with ammonium chloride solution (10 mL), then worked up with toluene (3 x 25 mL), washed with lithium chloride solution (5%, 2 x 40 mL), water (40 mL) and brine (40 mL).

Note that DCM dissolves the product better than toluene but makes it more difficult to wash.

KlementineJBS commented 9 months ago