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206251Attempts to the acid-mediated Pictet-Spengler cyclization of MW14 (MW28-1-80)
Experiments
profiles.google.com-micha.wolfleMichael Wolfle no conversion, starting material Trial 4: [b]MW14-3-79 [/b](50.0 mg, 194 µmol) was dissolved in trifluoroacetic acid (1 mL) and stirred at rt --> clear orange solution - after 16 h: brown solution, work-up TLC (EA:MeOH:TEA = 1:1:0.02) --> nearly complete conversion, less starting material 1H NMR: broad signals, unselective conversion, no starting material monitored Trial 5-7: [b]MW14-3-79[/b] (50.0 mg, 194 µmol) was dissolved in toluene (2 mL), p-TsOH (1, 2, 5 eq., see table) was added and stirred at rt First cloudy solutions, then brown precipitate - after 16 h: brown precipitate on the bottom of the vials, colorless precipitate on the wall, not soluble by heating TLC (EA:MeOH:TEA = 1:1:0.02) --> nearly complete conversion, less starting material, heterocyclic product ? Same Rf / stain color like cyclized amine 1H NMR: product with impurities, good conversion [data]104[/data][data]106[/data][data]108[/data] Work-up: - Basic work-up, 2 N NaOH solution, extraction with chloroform, dried over sodium sulfate TLC (EA:MeOH:TEA = 1:1:0.02) from the chloroform solutions, stain: Ceric ammonium molybdate [data=size:100x150]100[/data] [data=size:100x150]102[/data]]]>
Reaction Scheme


Table1


Hazard and Risk Assessment:
Reaction Class: 2
Hazards: X Irritant, C Corrosive, F Flammable
Risk rating: U = Unlikely

Start time (Trial 1-3): 18:35
Start time (Trial 4): 19:00
Start time (Trial 5-7): 19:30

End time: 10:00 26/05/2010

Trial 1-3:
MW14-3-79 (50.0 mg, 194 µmol) was dissolved in toluene (2 mL), phenylphosphinic acid (1, 2, 5 eq., see table) was added and stirred at rt
- 1,2 clear pale yellow solution; 3 cloudy pale yellow solution
- after 16 h: 1 and 3 cloudy solutions, get clear after heating, work-up
TLC (EA:MeOH:TEA = 1:1:0.02) --> no conversion, starting material

Trial 4:
MW14-3-79 (50.0 mg, 194 µmol) was dissolved in trifluoroacetic acid (1 mL) and stirred at rt --> clear orange solution
- after 16 h: brown solution, work-up
TLC (EA:MeOH:TEA = 1:1:0.02) --> nearly complete conversion, less starting material
1H NMR: broad signals, unselective conversion, no starting material monitored

Trial 5-7:
MW14-3-79 (50.0 mg, 194 µmol) was dissolved in toluene (2 mL), p-TsOH (1, 2, 5 eq., see table) was added and stirred at rt
First cloudy solutions, then brown precipitate
- after 16 h: brown precipitate on the bottom of the vials, colorless precipitate on the wall, not soluble by heating
TLC (EA:MeOH:TEA = 1:1:0.02) --> nearly complete conversion, less starting material, heterocyclic product ? Same Rf / stain color like cyclized amine
1H NMR: product with impurities, good conversion
1H NMR T5
1H NMR T6
1H NMR T7


Work-up:
- Basic work-up, 2 N NaOH solution, extraction with chloroform, dried over sodium sulfate

TLC (EA:MeOH:TEA = 1:1:0.02) from the chloroform solutions, stain: Ceric ammonium molybdate
TLC1
TLC2
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2066941Attempts to the acid-mediated Pictet-Spengler cyclization of MW14 (MW28-1-80)
Experiments
profiles.google.com-micha.wolfleMichael Wolfle no conversion, starting material Trial 4: [b]MW14-3-79 [/b](50.0 mg, 194 µmol) was dissolved in trifluoroacetic acid (1 mL) and stirred at rt --> clear orange solution - after 16 h: brown solution, work-up TLC (EA:MeOH:TEA = 1:1:0.02) --> nearly complete conversion, less starting material 1H NMR: broad signals, unselective conversion, no starting material monitored Trial 5-7: [b]MW14-3-79[/b] (50.0 mg, 194 µmol) was dissolved in toluene (2 mL), p-TsOH (1, 2, 5 eq., see table) was added and stirred at rt First cloudy solutions, then brown precipitate - after 16 h: brown precipitate on the bottom of the vials, colorless precipitate on the wall, not soluble by heating TLC (EA:MeOH:TEA = 1:1:0.02) --> nearly complete conversion, less starting material, heterocyclic product ? Same Rf / stain color like cyclized amine 1H NMR: product with impurities, good conversion [data]104[/data][data]106[/data][data]108[/data] Work-up: - Basic work-up, 2 N NaOH solution, extraction with chloroform, dried over sodium sulfate TLC (EA:MeOH:TEA = 1:1:0.02) from the chloroform solutions, stain: Ceric ammonium molybdate [data=size:100x150]100[/data] [data=size:100x150]102[/data]]]>
Reaction Scheme


Table1


Hazard and Risk Assessment:
Reaction Class: 2
Hazards: X Irritant, C Corrosive, F Flammable
Risk rating: U = Unlikely

Start time (Trial 1-3): 18:35
Start time (Trial 4): 19:00
Start time (Trial 5-7): 19:30

End time: 10:00 26/05/2010

Trial 1-3:
MW14-3-79 (50.0 mg, 194 µmol) was dissolved in toluene (2 mL), phenylphosphinic acid (1, 2, 5 eq., see table) was added and stirred at rt
- 1,2 clear pale yellow solution; 3 cloudy pale yellow solution
- after 16 h: 1 and 3 cloudy solutions, get clear after heating, work-up
TLC (EA:MeOH:TEA = 1:1:0.02) --> no conversion, starting material

Trial 4:
MW14-3-79 (50.0 mg, 194 µmol) was dissolved in trifluoroacetic acid (1 mL) and stirred at rt --> clear orange solution
- after 16 h: brown solution, work-up
TLC (EA:MeOH:TEA = 1:1:0.02) --> nearly complete conversion, less starting material
1H NMR: broad signals, unselective conversion, no starting material monitored

Trial 5-7:
MW14-3-79 (50.0 mg, 194 µmol) was dissolved in toluene (2 mL), p-TsOH (1, 2, 5 eq., see table) was added and stirred at rt
First cloudy solutions, then brown precipitate
- after 16 h: brown precipitate on the bottom of the vials, colorless precipitate on the wall, not soluble by heating
TLC (EA:MeOH:TEA = 1:1:0.02) --> nearly complete conversion, less starting material, heterocyclic product ? Same Rf / stain color like cyclized amine
1H NMR: product with impurities, good conversion
1H NMR T5
1H NMR T6
1H NMR T7


Work-up:
- Basic work-up, 2 N NaOH solution, extraction with chloroform, dried over sodium sulfate

TLC (EA:MeOH:TEA = 1:1:0.02) from the chloroform solutions, stain: Ceric ammonium molybdate
TLC1
TLC2
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