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181140-34-1 (R)-(-)-GLYCIDYL PHTHALIMIDE Application:181140-34-1 (R)-(-)-GLYCIDYL PHTHALIMIDE
2-[(2R)-3-bromo-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 18h; Product distribution / selectivity; | 90.6% |
With sodium methylate In methanol; toluene at 20℃; for 1.5h; Product distribution / selectivity; | 56.7% |
phthalimide
(R)-(-)-epichlorohydrin
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
Stage #1: phthalimide; (R)-(-)-epichlorohydrin With benzyltrimethylammonium chloride In isopropyl alcohol at 40℃; for 24h; Stage #2: With potassium tert-butylate In isopropyl alcohol at 20℃; for 3h; | 89% |
phthalimide
(R)-oxiranemethanol
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20 - 25℃; for 18h; | 86% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction; | 75% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Mitsunobu reaction; | |
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In dichloromethane at 20℃; Mitsunobu reaction; | |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Molecular sieve; |
phthalimide
(S)-epichlorohydrin
A
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With potassium fluoride on basic alumina In 2-methyltetrahydrofuran for 3h; Inert atmosphere; Reflux; stereospecific reaction; | A 11% B 85% |
phthalimide
(S)-epichlorohydrin
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With benzyltrimethylammonium chloride; sodium carbonate In tert-butyl alcohol at 20℃; for 23h; | 84% |
With benzyltrimethylammonium chloride In Isopropyl acetate at 20℃; for 72h; | 1.1 g |
2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With potassium tert-butylate In isopropyl alcohol at 15℃; for 4h; | 75% |
With potassium carbonate In toluene Reflux; | n/a |
(S)-epichlorohydrin
potassium phtalimide
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With benzyltrimethylammonium chloride In tert-butyl alcohol at 20℃; for 24h; | 72% |
(R)-(-)-epichlorohydrin
potassium phtalimide
A
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
B
(S)-N-glycidylphthalimide
Conditions | Yield |
---|---|
With benzyltrimethylammonium chloride In DMF (N,N-dimethyl-formamide) at 20℃; for 16h; |
phthalimide
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: aluminum oxide / 1-methyl-pyrrolidin-2-one / 64 - 68 °C 1.2: 0.5 h 2.1: potassium carbonate / toluene / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: aluminum oxide / 1-methyl-pyrrolidin-2-one / 64 - 68 °C 1.2: 0.5 h 2.1: potassium carbonate / toluene / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: aluminum oxide / 1-methyl-pyrrolidin-2-one / 64 - 68 °C 1.2: 0.5 h 2.1: potassium carbonate / toluene / Reflux View Scheme |
phthalimide
(R)-(-)-epichlorohydrin
A
2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione
B
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With aluminum oxide In 1-methyl-pyrrolidin-2-one at 64 - 68℃; |
2-oxiranylmethylisoindole-1,3-dione
A
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
B
(S)-N-glycidylphthalimide
Conditions | Yield |
---|---|
With Cu metal organic framework based on (R)-3,3′-bis(6-carboxy-2-naphthyl)-2,2′-dihydroxy-1,1′-binaphthyl*silica packed stainless steel column (10 cm long × 4.0 mm i.d.) In ethanol; hexane at 25℃; Resolution of racemate; |
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
2-[(2R)-3-bromo-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With hydrogen bromide In chloroform; water at 0℃; for 0.5h; | 96% |
Stage #1: (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione With iodobromomethane In 2-methyltetrahydrofuran at -78℃; for 0.0333333h; Stage #2: With methyllithium In 2-methyltetrahydrofuran; diethyl ether at -78℃; for 1h; enantioselective reaction; | 87% |
(1R,2S)-1-Amino-2-indanol
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
2-[(2R)-2-hydroxy-3-[[(1R,2S)-2-hydroxyindan-1-yl]amino]propyl] isoindoline-1,3-dione
Conditions | Yield |
---|---|
In isopropyl alcohol at 0℃; for 9h; Reflux; | 93% |
(S)-1-phenyl-ethylamine
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
2-[(2R)-2-hydroxy-3-[[(1S)-1-phenylethyl]amino]propyl]isoindoline-1,3-dione
Conditions | Yield |
---|---|
In isopropyl alcohol at 0℃; for 9h; Reflux; | 91% |
4-di[(2-hydroxyethyl)amino]-aniline
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
In ethanol at 75 - 85℃; for 24h; | 90% |
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
Stage #1: (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione With Chloroiodomethane In 2-methyltetrahydrofuran at -78℃; for 0.0333333h; Stage #2: With methyllithium In 2-methyltetrahydrofuran; diethyl ether at -78℃; for 1h; enantioselective reaction; | 90% |
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
Stage #1: (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione With diiodomethane In 2-methyltetrahydrofuran at -78℃; for 0.0333333h; Stage #2: With methyllithium In 2-methyltetrahydrofuran; diethyl ether at -78℃; for 1h; enantioselective reaction; | 89% |
4-Chloroguaiacol
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
(R)-1-(4-chloro-2-methoxyphenoxy)-3-phthalimido-2-propanol
Conditions | Yield |
---|---|
With cesium fluoride In DMF (N,N-dimethyl-formamide) at 80℃; for 38h; | 87% |
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 46h; | 59% |
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
In acetonitrile at 70℃; for 6h; | 84% |
1-(2-Methoxyphenyl)piperazine
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
(S)-(-)-1-phthaloylamino-3-[4-(2-methoxyphenyl)piperazin-1-yl]propan-2-ol
Conditions | Yield |
---|---|
In tetrahydrofuran for 72h; Heating; | 83% |
(R)-Phenylglycinol
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
2-[(2R)-2-hydroxy-3-[[(1R)-2-hydroxy-1-phenyl-ethyl]amino]propyl] isoindoline-1,3-dione
Conditions | Yield |
---|---|
In isopropyl alcohol at 0℃; for 9h; Reflux; | 83% |
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
In ethanol at 75 - 85℃; for 24h; | 80% |
(S)-N-benzyl-α-cyclohexylethylamine
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
In isopropyl alcohol for 13h; Cooling with ice; Reflux; regioselective reaction; | 77.66% |
(S)-1-phenyl-ethylamine
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
In isopropyl alcohol for 13h; Cooling with ice; Reflux; regioselective reaction; | 76.69% |
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With thiourea In methanol at 20℃; for 22h; | 74% |
[(1S)-1-cyclohexylethyl]amine
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
In isopropyl alcohol for 13h; Cooling with ice; Reflux; regioselective reaction; | 73.07% |
(2R)-2-aminobutan-1-ol
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
2-[(2R)-2-hydroxy-3-[[(1R)-1-(hydroxymethyl)propyl]amino]propyl] isoindoline-1,3-dione
Conditions | Yield |
---|---|
In isopropyl alcohol at 0℃; for 9h; Reflux; | 73% |
carbon dioxide
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With C25H22OP(1+)*Br(1-) In chlorobenzene at 120℃; under 760.051 Torr; for 12h; | 73% |
3,6-dibromo-9H-carbazole
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
Stage #1: 3,6-dibromo-9H-carbazole With caesium carbonate In N,N-dimethyl-formamide at 30℃; for 1h; Stage #2: (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione In N,N-dimethyl-formamide at 30℃; for 15h; | 72% |
(S)-1-(1-Naphthyl)ethylamine
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
In isopropyl alcohol for 13h; Cooling with ice; Reflux; regioselective reaction; | 72% |
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
(R)2-(oxiran-2-ylmethyl)isoindolin-1-one
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; Inert atmosphere; | 70% |
(1R,2R)-N,N'-dibenzylcyclohexane-1,2-diamine
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
In isopropyl alcohol for 13h; Cooling with ice; Reflux; regioselective reaction; | 70% |
[(1R)-1-cyclohexylethyl]amine
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
In isopropyl alcohol for 13h; Cooling with ice; Reflux; regioselective reaction; | 68% |
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
4-(4-aminophenyl)morpholin-3-one
Conditions | Yield |
---|---|
In ethanol for 24h; Reflux; | 60% |
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