KBS11-5 - Azidation of 1-bromoadamantane about usyd_phd_eln

[KlementineJBS]

28.04.22

• 105.2 mg (0.489 mmol) of 1-bromoadamantane dissolved in 3 mL DMF
• added 0.15 mL (1.14 mmol, 2.3 equiv.) TMSN3 and 0.14 mL SnCl4 (1 M in heptane, 0.3 equiv.)
• heated to 60 C and left stirring at 12.15 pm

[KlementineJBS]

29.04.22

TLC'd at 9.30am in various eluents/stains. Best result in 40% ethyl acetate with Goofy's stain, as vanillin fails to show starting material.

Assigned top spots as starting material - highest spot believed to be some kind of impurity in SM. Large spots (UV active) towards bottom believed to be desired compound.

Took reaction off at 4.30 pm after TLC indicated no SM remaining.

Quenched on ice with 15 mL water.

Extracted with ethyl acetate (30 mL) and washed with water (5 x 6 mL) to remove DMF.

[KlementineJBS]

02.05.22

Rotovapped organic layer and NMR'd.

KBS11-5 crude_1.zip

Appears to be mostly starting material - compare superimposed images of KBS11-5 (blue, faint) and KBS11-1 in first photo vs SM (blue, faint) and KBS11-1 in second photo.

KBS11-5 and KBS11-1

SM and KBS11-1