KBS11-4 - Azidation of 1-bromoadamantane about usyd_phd_eln

[KlementineJBS]

19.04.22

• Monitor closely and consider adding extra TMSN3
• Attempt alternative purification?

[KlementineJBS]

20.04.22

• 496.8 mg (2.31 mmol) 1-bromoadamantane added to oven-dried flask under positive pressure
• 9 mL dry THF added
• 0.6 mL (4.56 mmol, 2equiv.) TMSN3 added
• 0.7 mL (0.3 equiv.) SnCl4 added at 10.15 am
• heated to reflux and left
• TLC'd at 4.30 pm (20:80 EtOAc:hexane)

• added more TMSN3 (0.3 mL, 2.28 mmol, 1 equiv.)

[KlementineJBS]

21.04.22

• TLC'd at 9.45 am

• TLC'd again at 4.30 pm (10% EtOAc in hexane)

• confused by spots

[KlementineJBS]

22.04.22

• TLC'd at 9.30 am (10:90 EtOAc:hexane)

• decided to quench reaction anyway - added 50 mL water dropwise

• extracted with ethyl acetate (3 X 40 mL) and washed with brine (100 mL)

• dried over mag sulphate

• vial (empty) = 15.4911 g

[KlementineJBS]

26.04.22

NMR of crude product

KBS11-4 cr_1.zip

• tried to column crude product
• initially ran on ethyl acetate by mistake for ~1.5 CV
• then ran on 100% pet. benzine

[KlementineJBS]

29.04.22

Ran a second column (gradient from 0 - 40% ethyl acetate in hexane). Product only evident in fractions 10 and 11.

Unfortunately, NMR indicated little or no desired product was present.

KBS11-4 columned_1.zip