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CAS No.: | 66673-40-3 |
---|---|
Name: | 5-Hydroxymethylpyrrolidin-2-one |
Article Data: | 24 |
Molecular Structure: | |
Formula: | C5H9NO2 |
Molecular Weight: | 115.132 |
Synonyms: | 2-Pyrrolidinone,5-(hydroxymethyl)-, (R)-;(-)-5-(Hydroxymethyl)-2-pyrrolidinone;(5R)-5-Hydroxymethylpyrrolidin-2-one;(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone;(R)-5-(Hydroxymethyl)pyrrolidin-2-one;(R)-5-Hydroxymethyl-2-pyrrolidinone;(R)-5-Hydroxymethyl-2-pyrrolidone;(R)-5-Hydroxymethylpyrrolidin-2-one;(R)-5-Oxopyrrolidine-2-methanol;(R)-(-)-5-hydroxymethyl-2-pyrrolidinone; |
EINECS: | -0 |
Density: | 1.153 g/cm3 |
Melting Point: | 83-85 °C(lit.) |
Boiling Point: | 346 °C at 760 mmHg |
Flash Point: | 163 °C |
Appearance: | White powder |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 26-36 |
PSA: | 49.33000 |
LogP: | -0.41390 |
(R)-5-hydroxymethylpyrrolidin-2-one
Conditions | Yield |
---|---|
With water; trifluoroacetic acid In dichloromethane at 50℃; for 5h; | 99% |
methyl (2R)-pyroglutamate
(R)-5-hydroxymethylpyrrolidin-2-one
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate at 0℃; | 97% |
With methanol; sodium tetrahydroborate at 0℃; | 97% |
With methanol; sodium tetrahydroborate at 0℃; | 97% |
ethyl (R)-2-pyrrolidone-5-carboxylate
(R)-5-hydroxymethylpyrrolidin-2-one
Conditions | Yield |
---|---|
With lithium borohydride In tetrahydrofuran for 16h; Ambient temperature; | 85% |
With sodium tetrahydroborate In tetrahydrofuran; methanol at 5℃; for 1h; | 80% |
With sodium tetrahydroborate In ethanol for 2h; Ambient temperature; | 79% |
D-pyrrolidone-5-carboxylic acid
(R)-5-hydroxymethylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 94 percent / SOCl2 / 1.5 h / 80 °C 2: 85 percent / LiBH4 / tetrahydrofuran / 16 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: 95 percent / thionyl chloride / 1.) 0 deg C, 30 min, 2.) room temp., 3 h 2: 78 percent / NaBH4 / ethanol / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: SOCl2 / 48 h / Ambient temperature; pH=0 2: 58 percent / NaBH4 / propan-2-ol / 20 h / Ambient temperature View Scheme |
D-Glutamic acid
(R)-5-hydroxymethylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1) thionyl chloride / 1a) room temp., 1 h, 1b) reflux, 30 min. 2: 32.5 g / 1.5 h / 150 °C / 15 Torr 3: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: 88 percent / SOCl2, KOH / 150 °C 2: LiBH4 View Scheme | |
Multi-step reaction with 3 steps 1: H2O / 63 h / Heating 2: SOCl2 / 48 h / Ambient temperature; pH=0 3: 58 percent / NaBH4 / propan-2-ol / 20 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1.1: thionyl chloride 1.2: Amberlyst A-21 1.3: Reflux 2.1: sodium tetrahydroborate / isopropyl alcohol View Scheme | |
Multi-step reaction with 2 steps 1.1: thionyl chloride / 20 h / 20 °C 1.2: 2 h / Reflux 2.1: sodium tetrahydroborate / isopropyl alcohol / 20 h / 20 °C View Scheme |
D-glutamic acid diethyl ester
(R)-5-hydroxymethylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 32.5 g / 1.5 h / 150 °C / 15 Torr 2: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature View Scheme |
D-glutamic acid dimethyl ester hydrochloride
(R)-5-hydroxymethylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: toluene / 4 h / Reflux 2: isopropyl alcohol; sodium tetrahydroborate / 20 h / 20 °C View Scheme |
(R)-5-hydroxymethylpyrrolidin-2-one
tert-butyldimethylsilyl chloride
(R)-5-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 20℃; for 4h; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide for 24h; Ambient temperature; | 99% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; | 99% |
(R)-5-hydroxymethylpyrrolidin-2-one
methyl 3'-(cyanocarbonyl)-2,2'-binaphthalene-3-carboxylate
Conditions | Yield |
---|---|
With dmap In acetonitrile at 14℃; for 1.5h; | 100% |
(R)-5-hydroxymethylpyrrolidin-2-one
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 1.5h; Dean-Stark; Reflux; | 100% |
With camphor-10-sulfonic acid at 75℃; for 20h; Reagent/catalyst; Temperature; Time; Concentration; | 78% |
With camphor-10-sulfonic acid at 75℃; for 20h; Time; Temperature; Reflux; | 78% |
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