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31st May 2012 @ 05:18
Repeat of MNR35-2 on a 900 mg scale

Repeat Preparation of MNR35-2 - Step 2 in the alternative route to MNR26

MNR35-3%20scheme.png

mnr35-3%20table.PNG

Hazard and Risk Assessment:
MNR35

Procedure

To a solution of MNR34-2 (0.900 g, 3.49 mmol) in toluene (35 ml) was added 2,2-Diethoxyethylamine (0.86 mL, 6.98 mmol), and the mixture was heated to reflux for 2 hours during which time the reaction mixture turned from clear to yellow. The reaction was then allowed to cool to room temperature then cooled in an icebath. Again, as before, nothing crashed out so the mixture was concentrated and left in the freezer over the weekend.

Column 0-10% MeOH/EtOAc+0.1%TEA
Attached Files
29th May 2012 @ 04:42
MNR26-3%20scheme.png
mnr26-3%20table.PNG

Hazard and Risk Assessment:
HIRAC MNR26-3.pdf


Procedure:
MNR35-2 (0.5 g, 0.19 mmol) in toluene (2 mL) was treated with methanesulfonic acid (0.05 mL, 0.37 mmol) and the reaction was heated to reflux for 3 hours by which time TLC had shown complete consumption of SM.

Crude - 0.045 g as a dark brown oil
Attached Files
29th May 2012 @ 03:04
MNR36-1%20scheme.png

mnr36-1%20table.PNG

Hazard and Risk Assessment:
MNR34

Procedure

2-phenethylamine (7.0 mL, 55.57 mmol) and NaHCO3 (4.67 g, 55.57 mmol) were dissolved in DCM (70 mL) at room temperature under argon. The mixture was cooled to 0 °C and chloroacetyl chloride (5.30 mL, 66.68 mmol) was added dropwise - Upon addition a white precipitate formed and the reaction stopped stirring, DCM (40 mL) was added to free up this solid and to allow stirring to continue. The reaction mixture was stirred at 0 °C for 3 hours. Water (50 mL) was slowly added and the aqueous phase was extracted with DCM (100 mL). The organic layers were combined, washed with HCl (2M , 50 mL), dried with MgSO4, filtered, concentrated, and dried under vacuum to give grey/off white crystals. The crude was recrystallised with EtOH/hexane and washed with hexane to give fine off white crystals.

1st crop 4.515 g, 22.8 mmol, 41 % as off white crystals

2nd crop 2.590 g, 13.1 mmol, 24 %

1H NMR
13C NMR

mnr36-1_1st.zip
Attached Files
29th May 2012 @ 03:00
Preparation of MNR34-1 - Step 1 in the alternative route to MNR26

MNR34-1%20scheme.png

mnr34-2%20table.PNG

Hazard and Risk Assessment:
MNR34

Procedure

3,4-dimethoxyphenethylamine (8 mL, 48.17 mmol) and NaHCO3 (4.05 g, 48.17 mmol) were dissolved in DCM (60 mL) at room temperature under argon. The mixture was cooled to 0 °C and chloroacetyl chloride (4.05 mL, 48.17 mmol) was added dropwise. The reaction mixture was stirred at 0 °C for 2 hours. Water (50 mL) was slowly added and the aqueous phase was extracted with DCM (100 mL). The organic layers were combined, washed with an aqueous solution of HCl (2M , 50 mL), dried with MgSO4, filtered, concentrated,and dried under vacuum. The crude off white solid was obtained and was recrystalised with EtOH/Hexane. The white crystals were washed with hexane to give fine white crystals.

1st crop 6.352 g, 24.65 mmol, 51 % as fine white crystals

2nd crop 1.017 g, 3.95 mmol, 8 % as fine white crystals

1H NMR

mnr34-2_1st.zip
Attached Files
25th May 2012 @ 03:16
Repeat of MNR35-1 using only recrystalised starting material (MNR34-1)

Preparation of MNR35-1 - Step 2 in the alternative route to MNR26
Preparation of MNR34-1 - Step 1 in the alternative route to MNR26

MNR35-1%20scheme.png

mnr35-2%20table.PNG

Hazard and Risk Assessment:
MNR35

Procedure

To a solution of MNR34-1 (0.048 g, 0.19 mmol) in toluene (2 ml) was added 2,2-Diethoxyethylamine (0.05 mL, 0.37 mmol), and the mixture was heated to reflux for 2 hours during which time the reaction mixture turned from clear to yellow. The reaction was then allowed to cool to room temperature then cooled in an icebath. Again, as before, nothing crashed out so the mixture was concentrated and left in the freezer over the weekend.

Monday: Column 0-10% MeOH/EtoAC+0.1%TEA

Frac 25-39 - 0.061 g, 0.17 mmol, 92%

mnr35-2_frac26-39.pdf
mnr35-2_frac26-39_13C.pdf
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Attached Files