KBS26-1 - Deprotection of bis-adamantyl 1,6-diaminohexane about usyd_phd_eln

[KlementineJBS]

15.11.22

1. Set up a flask in an ice bath and added HCl in dioxane (4.0 M in 1,4-dioxane, 1 mL, 4.00 mmol)
2. Added KBS22-1 (86.1 mg, 0.115 mmol) in 1,4-dioxane (1.5 mL) at 10.49 am
3. Removed ice bath and left stirring from 11 am
4. TLC'd at 11.50 am and found reaction had gone to completion

Solvent is NH4OH:MeOH:DCM = 1:9:90

Empty vial: 15.8197
Full vial: 15.9098
Mass: 90 mg (0.146 mmol)

[KlementineJBS]

21.11.22

LRMS

KBS26-1 cr.pdf
KBS26-1 v3.d.zip

Evidence of compound - 547.40 [M+H]+. Relatively clean - 377 and 731 peaks are remnants of previous runs.

H NMR

KBS26-1 crude_1.zip

KBS26-1 cr.pdf

Hydrochloride salt - gives poor resolution.

[KlementineJBS]

29.11.22

Separated HCl salt - retained some in a vial (weight = 15.8403, mass of HCl salt = 17.9 mg) and set aside 38.4 mg to convert to free base.

1. Rinsed a spatula-ful of Ambersep 900 hydroxide form resin with methanol (3 x 5 mL)
2. Pre-swelled with methanol for 1 hr (8 mL)
3. Added KBS26-1 (38.4 mg, 0.062 mmol) dissolved in methanol (10 mL)
4. Left stirring for ~1 hr
5. Collected by vacuum filtration (Buchner funnel)
6. Rotovapped down

Empty vial: 15.6620
Full vial: 15.6914
Mass: 29.4 mg (0.053 mmol), 87%

[KlementineJBS]

HPLC - LRMS

KBS26-1 prep F11.pdf
KBS26-1 prep F10.pdf
KBS26-1 prep F9.pdf
KBS26-1 prep F2.pdf

[KlementineJBS]

IR

KBS26-1.zip
KBS26-1 26-06-24.pdf

[KlementineJBS]

[KlementineJBS]

[KlementineJBS]

[KlementineJBS]

KBS26-1 prepped.pdf
KBS26-1 prepped.d.zip