KBS21-1 - Propargylation of 1,8-diaminooctane about usyd_phd_eln

[KlementineJBS]

01.08.22

1. Added NaH (407 mg, 17.0 mmol) to a dry flask under nitrogen
2. Added KBS20 (413.6 mg, 1.20 mmol) by solution transfer (15 mL dry DMF)
3. Added propargyl bromide (2.84 mmol) and left stirring from 4pm

[KlementineJBS]

02.08.22

TLC at 3 pm indicated some reaction had occurred. Reaction mixture had also turned black, which previously has indicated that reaction is progressing (see #23).

Left stirring a little longer.

[KlementineJBS]

03.08.22

TLC at 12 indicated reaction was still not complete. However, this reaction typically does not go to completion, so the decision was made to work it up anyway.

4. Diluted with ammonium chloride (15 mL) and water (45 mL)
5. Extracted with toluene (3 x 40 mL)
6. Washed with water to remove DMF (3 x 100 mL)
7. Brine wash (120 mL)
8. Dried over MgSO4 and rotovapped down

[KlementineJBS]

04.08.22

Empty vial: 15.8923
Full vial: 16.2472
Mass: 354.9 mg

(Crystals formed in RBF when left overnight)

H NMR

1H NMR (300 MHz, CDCl3) δ 4.49, 4.00, 3.29, 3.10, 3.08, 2.18, 1.46, 1.44, 1.29, 1.25.

KBS21-1_1.zip

KBS21-1 cr processed.pdf

Appears to be a mixture of both mono and bis products, as expected. Will confirm with mass spec and likely column manually as with #22.

[KlementineJBS]

05.08.22

KBS21-1 cr.pdf

[KlementineJBS]

08.08.22

Fractions	Empty vial	Full vial	Mass (mg)	Moles (mmol)	Yield (%)	Compound
2 - 5	16.0268	16.1272	-	-	-	-
12 - 14	15.9860	15.9863	-	-	-	-
16 - 20	15.7857	15.7973	11.6	-	-	-
21 - 24	16.0074	16.0565	49.1	-	-	-
25 - 27	16.0780	-	-	-	-	-
28	15.8620	16.1607	298.7	-	-	-

[KlementineJBS]

11.08.22

KBS21-1 F21-24.pdf
KBS21-1 F28.pdf
KBS21-1 F25-27.pdf
KBS21-1 F28.d.zip
KBS21-1 F21-24.d.zip
KBS21-1 F25-27.d.zip