Conditions |
Yield |
With
oxalyl dichloride; dimethyl sulfoxide;
In
triethylamine;
|
100%
|
With
pyridine-SO3 complex; triethylamine;
In
dimethyl sulfoxide;
|
100%
|
With
Dess-Martin periodane; tert-butyl alcohol;
In
dichloromethane;
Ambient temperature;
|
99%
|
With
2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium bromide;
sodium hydrogencarbonate;
In
dichloromethane; water;
|
99%
|
With
[bis(acetoxy)iodo]benzene; BF4(1-)*C19H32N6O2(1+);
In
dichloromethane;
at 20 ℃;
for 0.166667h;
|
98%
|
With
1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I)tetrafluoroborate;
In
acetonitrile;
for 21h;
Heating;
|
98%
|
With
1,10-Phenanthroline; potassium tert-butylate; copper(l) chloride;
dibenzyl azodicarboxylate; oxygen;
In
fluorobenzene;
Heating;
|
97%
|
With
di-tert-butyl-diazodicarboxylate; potassium tert-butylate; oxygen;
1,10-Phenanthroline; copper(l) chloride;
In
fluorobenzene;
Heating;
|
97%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 0 ℃;
for 1h;
|
97.6%
|
With
2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid;
In
dichloromethane;
at 0 - 20 ℃;
|
96%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 20 ℃;
for 16h;
|
96%
|
With
sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at 10 - 20 ℃;
for 0.166667h;
|
95%
|
With
oxalyl dichloride; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at -78 ℃;
|
95%
|
N-(tert-butoxycarbonyl)-L-prolinol;
With
oxalyl dichloride; dimethyl sulfoxide;
In
dichloromethane;
at -78 ℃;
With
triethylamine;
In
dichloromethane;
at -78 ℃;
|
95%
|
With
oxalyl dichloride; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at -78 ℃;
|
95%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 20 ℃;
for 2.16667h;
|
95%
|
N-(tert-butoxycarbonyl)-L-prolinol;
With
oxalyl dichloride; dimethyl sulfoxide;
In
dichloromethane;
at -78 ℃;
for 1h;
Inert atmosphere;
With
triethylamine;
In
dichloromethane;
at -78 - 20 ℃;
Inert atmosphere;
|
94%
|
N-(tert-butoxycarbonyl)-L-prolinol;
With
dimethyl sulfoxide; triethylamine;
at 5 - 10 ℃;
for 0.25h;
With
sulfur trioxide pyridine complex;
at 0 ℃;
for 2h;
|
94%
|
N-(tert-butoxycarbonyl)-L-prolinol;
With
oxalyl dichloride;
In
dichloromethane; dimethyl sulfoxide;
at -78 ℃;
for 1.08333h;
Inert atmosphere;
With
N-ethyl-N,N-diisopropylamine;
In
dichloromethane; dimethyl sulfoxide;
at 20 ℃;
for 0.75h;
Inert atmosphere;
|
94%
|
With
sulfur trioxide pyridine complex; triethylamine;
In
dimethyl sulfoxide;
for 2h;
Ambient temperature;
|
93%
|
With
Dess-Martin periodane;
In
dichloromethane;
for 2h;
Ambient temperature;
|
92%
|
With
sodium hypochlorite; TEMPO; sodium hydrogencarbonate; sodium bromide;
In
dichloromethane;
at 0 ℃;
for 1h;
|
92%
|
With
sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; chlorine; sodium hydrogencarbonate; sodium bromide;
In
dichloromethane;
at 0 ℃;
for 1h;
|
92%
|
With
sodium hypochlorite; sodium hydrogencarbonate; sodium bromide;
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;
In
dichloromethane;
at 0 ℃;
for 1h;
|
92%
|
With
oxalyl dichloride; dimethyl sulfoxide;
In
dichloromethane;
|
92%
|
N-(tert-butoxycarbonyl)-L-prolinol;
With
1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(actonitrile)copper(I) hexafluorophosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;
In
acetonitrile;
at 50 ℃;
for 16h;
With
1,4-bis(3-isocyanopropyl)piperazine;
In
dichloromethane;
at 20 ℃;
for 0.166667h;
|
91%
|
With
2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid;
In
dichloromethane;
at 0 - 20 ℃;
|
88.8%
|
With
pyridine-SO3 complex; triethylamine;
In
dimethyl sulfoxide;
at 7 - 8 ℃;
for 2.5h;
|
87%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 20 ℃;
|
87%
|
With
sodium hypochlorite solution; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide;
In
dichloromethane; water;
at 0 ℃;
|
86%
|
With
phosgene; dimethyl sulfoxide; triethylamine;
|
85%
|
With
pivaloyl chloride; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at -78 - 20 ℃;
for 1h;
|
85%
|
With
Oxone; sodium ortho-iodobenzenesulfonate; sodium sulfate;
In
ethyl acetate;
at 70 ℃;
for 8h;
Inert atmosphere;
|
85%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 20 ℃;
for 3h;
|
85%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 0 - 20 ℃;
for 3h;
|
85%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 20 ℃;
for 1h;
|
83%
|
With
1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(actonitrile)copper(I) hexafluorophosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;
In
acetonitrile;
|
83%
|
With
1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
acetonitrile;
for 0.5h;
Inert atmosphere;
Reflux;
|
83%
|
With
sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide;
In
water; ethyl acetate; toluene;
at 0 ℃;
for 0.166667h;
|
82%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 0 - 20 ℃;
for 2h;
|
82%
|
With
pyridine-SO3 complex; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
|
81%
|
N-(tert-butoxycarbonyl)-L-prolinol;
With
triethylamine;
In
dimethyl sulfoxide;
for 0.25h;
With
sulfur trioxide pyridine complex;
In
dimethyl sulfoxide;
at 20 ℃;
for 3.16667h;
Cooling with ice;
|
81%
|
N-(tert-butoxycarbonyl)-L-prolinol;
With
triethylamine;
In
dimethyl sulfoxide;
for 0.25h;
With
sulfur trioxide pyridine complex;
In
dimethyl sulfoxide;
at 20 ℃;
for 2.5h;
Cooling with ice;
|
81%
|
N-(tert-butoxycarbonyl)-L-prolinol;
With
triethylamine;
In
dimethyl sulfoxide;
for 0.25h;
With
sulfur trioxide pyridine complex;
In
dimethyl sulfoxide;
at 20 ℃;
for 3.16667h;
Cooling with ice;
|
81%
|
N-(tert-butoxycarbonyl)-L-prolinol;
With
triethylamine;
In
dimethyl sulfoxide;
for 0.25h;
Cooling with ice;
With
sulfur trioxide pyridine complex;
In
dimethyl sulfoxide;
at 20 ℃;
for 2.5h;
|
81%
|
N-(tert-butoxycarbonyl)-L-prolinol;
With
triethylamine;
In
dimethyl sulfoxide;
for 0.25h;
With
sulfur trioxide pyridine complex;
at 20 ℃;
for 2.5h;
|
81%
|
N-(tert-butoxycarbonyl)-L-prolinol;
With
triethylamine;
In
dimethyl sulfoxide;
for 0.25h;
With
sulfur trioxide pyridine complex;
In
dimethyl sulfoxide;
at 20 ℃;
for 3.16667h;
Cooling with ice;
|
81%
|
With
sulfur trioxide pyridine complex; triethylamine;
In
dimethyl sulfoxide;
at 20 ℃;
for 3.41667h;
Cooling with ice;
|
81%
|
With
oxygen; potassium carbonate;
CuCl*Phen; dibenzyl azodicarboxylate;
In
fluorobenzene;
at 80 ℃;
|
80%
|
With
pyridinium chlorochromate;
In
dichloromethane;
for 3h;
|
80%
|
With
4 A molecular sieve; P(p-CH3OC6H4)3; 4-methylmorpholine N-oxide;
In
dichloromethane;
at 20 ℃;
for 1h;
|
80%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 0 - 20 ℃;
Inert atmosphere;
|
80%
|
With
pyridium chlorochromate;
|
79%
|
With
pyridine-SO3 complex; triethylamine;
In
dichloromethane; dimethyl sulfoxide;
at 0 ℃;
for 1h;
|
77%
|
With
pyridinium chlorochromate;
In
dichloromethane;
at 20 ℃;
Molecular sieve;
|
76%
|
With
pyridinium chlorochromate;
In
dichloromethane;
at 20 ℃;
Molecular sieve;
|
76%
|
With
pyridine-SO3 complex; triethylamine;
In
dimethyl sulfoxide;
at 20 ℃;
|
75%
|
With
1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
ethyl acetate;
Heating;
|
74%
|
With
silica gel; pyridinium chlorochromate;
In
dichloromethane;
at 20 ℃;
for 3h;
|
71%
|
N-(tert-butoxycarbonyl)-L-prolinol;
With
oxalyl dichloride; dimethyl sulfoxide;
In
dichloromethane;
at -78 ℃;
for 1.25h;
With
N-ethyl-N,N-diisopropylamine;
In
dichloromethane;
at 20 ℃;
|
58.8%
|
N-(tert-butoxycarbonyl)-L-prolinol;
With
oxalyl dichloride; dimethyl sulfoxide;
In
dichloromethane;
for 0.75h;
Cooling with dry ice;
With
triethylamine;
In
dichloromethane;
at 0 ℃;
for 1h;
Cooling with dry ice;
|
55.4%
|
N-(tert-butoxycarbonyl)-L-prolinol;
With
oxalyl dichloride; dimethyl sulfoxide;
In
dichloromethane;
for 0.75h;
Cooling with ice;
Inert atmosphere;
With
triethylamine;
In
dichloromethane;
at 0 ℃;
for 1h;
Inert atmosphere;
|
55.4%
|
With
sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at -10 - 20 ℃;
for 16h;
|
55%
|
With
pyridinium chlorochromate;
In
hexane; dichloromethane; ethyl acetate;
|
52.9%
|
N-(tert-butoxycarbonyl)-L-prolinol;
With
oxalyl dichloride;
In
dichloromethane; dimethyl sulfoxide;
at -78 ℃;
for 0.333333h;
With
triethylamine;
In
dichloromethane; water; dimethyl sulfoxide;
at 25 ℃;
for 0.0833333h;
|
52%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 0 - 20 ℃;
for 2h;
|
50.7%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 0 - 20 ℃;
for 2h;
Inert atmosphere;
Sealed tube;
|
50.7%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 0 - 20 ℃;
for 2h;
|
50.7%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 0 - 20 ℃;
for 2h;
|
50.7%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 0 - 20 ℃;
for 2h;
|
50.7%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 0 - 20 ℃;
for 2h;
|
50.7%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 0 - 20 ℃;
for 2h;
|
50.7%
|
With
Dess-Martin periodane;
In
dichloromethane;
at 0 - 20 ℃;
for 2h;
|
50.7%
|
With
lithium tetrafluoroborate; tert.-butylnitrite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;
In
dichloromethane;
Reagent/catalyst;
Inert atmosphere;
Reflux;
|
42%
|
With
sodium carbonate; pyridinium chlorochromate;
In
dichloromethane;
at 20 ℃;
for 6h;
|
36%
|
With
4 A molecular sieve; acetic acid; pyridinium chlorochromate;
In
dichloromethane; water;
for 2h;
Ambient temperature;
|
|
With
oxalyl dichloride; dimethyl sulfoxide; triethylamine;
Multistep reaction;
1) THF, 2h, -70 deg C 2) 15 min, -70 deg C;
|
|
With
sulfur trioxide pyridine complex; triethylamine;
In
dimethyl sulfoxide;
for 0.166667h;
Ambient temperature;
|
|
With
oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
Yield given. Multistep reaction;
1) CH2Cl2, -63 deg C, 30 min, 2) up to r.t., 30 min;
|
|
With
pyridine-SO3 complex; triethylamine;
In
dichloromethane; dimethyl sulfoxide;
for 0.166667h;
Ambient temperature;
|
|
With
oxalyl dichloride;
In
dichloromethane; dimethyl sulfoxide;
at -78 ℃;
for 0.333333h;
|
|
With
sulfur trioxide pyridine complex;
In
dimethyl sulfoxide;
|
|
With
4-methyl-morpholine; oxalyl dichloride; dimethyl sulfoxide;
In
dichloromethane;
at -65 - 0 ℃;
|
|
With
pyridine-SO3 complex; triethylamine;
In
dimethyl sulfoxide;
1.) 0 deg C, 1 h; 2.) 0-10 deg C, 2.5 h;
|
|
With
oxalyl dichloride; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at -63 ℃;
Yield given;
|
|
In
dichloromethane;
Swern oxidation;
|
|
|
|
With
oxalyl dichloride; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at -78 - 20 ℃;
for 0.583333h;
|
|
|
|
With
Dess-Martin periodane;
In
dichloromethane;
at 20 ℃;
|
|
With
oxalyl dichloride; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at -50 ℃;
for 0.5h;
|
|
With
4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; sodium hypochlorite; sodium bromide;
sodium hydrogencarbonate;
In
ethyl acetate; toluene;
at 0 ℃;
for 1.25h;
|
|
With
Dess-Martin periodane;
In
dichloromethane;
|
|
With
oxalyl dichloride; dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at -63 ℃;
|
|
With
pyridine-SO3 complex; triethylamine;
In
dimethyl sulfoxide;
at 5 ℃;
for 2.5h;
|
|
With
pyridine; sulfur trioxide; N-ethyl-N,N-diisopropylamine;
In
dichloromethane; dimethyl sulfoxide;
at -5 ℃;
for 5h;
|
|
With
2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid;
In
dichloromethane;
at 20 ℃;
for 0.25h;
|
70 % Turnov.
|
With
dipyridinium dichromate;
|
|
With
oxalyl dichloride; TEA; dimethyl sulfoxide;
In
dichloromethane;
at -78 - 0 ℃;
|
|
With
dimethyl sulfoxide; triethylamine;
In
dichloromethane;
at -63 ℃;
|
|