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CAS No. : | 56613-80-0 | MDL No. : | MFCD00008062 |
Formula : | C8H11NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IJXJGQCXFSSHNL-QMMMGPOBSA-N |
M.W : | 137.18 | Pubchem ID : | 2724025 |
Synonyms : |
(R)-(-)-2-Phenylglycinol
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With caesium carbonate; In dimethylsulfoxide-d6; at 25 - 150℃; under 3800.26 Torr; for 24h;Schlenk technique; Autoclave; | General procedure: To a DMSO-d6 (1 mL) solution of cesium carbonate (33 mg, 0.1 mmol) in a Teflon tube was added (S)-1b (78 muL, 1 mmol). The Teflon tube containing the reaction mixture was fitted into a 30 mL autoclave. The autoclave was frozen with liquid nitrogen (?196 °C) prior to connecting to a vacuum line for air removal. After the mixture was evaporated under vacuum at ?196 °C and warmed up to room temperature, CO2 was filled into the autoclave (3 atm). The autoclave was stirred at 150 °C for 24 h. Upon completion, the reaction mixture was subjected to 1H NMR for crude product yield determination, which calculated based on the ratio between product and internal standard (N,N-dimethylformamide). After that, DMSO-d6 was removed through distillation under vacuum conditions; the syrupy product was then purified by column chromatography on silica gel (hexane/ethyl acetate 3:1) to give the product (S)-4-methyloxazolidin-2-one (S)-2b as colorless oil with an isolated yield of 36percent (36.4 mg, 0.36 mmol). |
Yield | Reaction Conditions | Operation in experiment |
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24% | With N-ethyl-N,N-diisopropylamine; In acetonitrile; | To a solution of phenylbromoacetate (18.58 g, 86 mmol) in CH3CN under nitrogen was added a solution of (R)-phenylglycinol (10.17 g, 74 mmol) and di-isopropylethylamine (34 ml_, 195 mmol) in CH3CN. The volatiles were removed under reduced pressure keeping the bath temperature below 25 0C to obtain an oil that was treated with EtOAc (120 mL) and stirred for 15 min. The resulting white precipitate was removed by filtration. The filtrate was concentrated under reduced pressure and the desired product was isolated using column chromatography (SiO2) with a step gradient of 10 percent to 50 percent [v/v] EtOAc in cyclohexane to give after evaporation (f?)-5-phenylmorpholin-2- one EBE 06134 (3.17 g, 24 percent yield) as a white solid.MW: 177.2; Yield: 24 percent; White Solid; Mp (0C): 50.3Rf\\ 0.30 (EtOAc:cyclohexane = 50:50). 1H-NMR (CDCI3, delta): 1.99 (s, 1 H, NH), 3.89 (q, 2H, J = 17.8 Hz, N-CH2), 4.18(dd, 1 H, J = 3.7 Hz, J = 10.3 Hz, 0-CH), 4.29 (t, 1 H, J = 10.5 Hz, N-CH), 4.40(dd, 1 H, J = 3.7 Hz, J = 10.5 Hz, 0-CH), 7.30-7.45 (m, 5H, ArH).13C-NMR (CDCI3, delta): 46.8, 54.8, 72.8, 125.3 (2xC), 127.0, 127.3 (2xC), 135.9,166.0. [G]22D = + 30.3 ° (c = 1.00, MeOH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5% | In chlorobenzene Heating; |
Yield | Reaction Conditions | Operation in experiment |
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56% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chloro-trimethyl-silane; sodium chloride; sodium hydrogencarbonate; triethylamine; In dichloromethane; | Reference Example 4 (2R)-2-Octylsulfonylamino-2-phenylethanol To a solution of (2R)-2-amino-2-phenylethanol (960 mg) in methylene chloride (30 ml) was added triethylamine (2.0 ml) and the mixture was cooled to -78 C. To the mixture was added dropwise chlorotrimethylsilane (0.90 ml), the mixture was stirred for 3 hours at -78 C. and then stirred for 1 hour at 0 C. The reaction mixture was cooled to -78 C. again. To the mixture was added dropwise <strong>[7795-95-1]1-octanesulfonyl chloride</strong> (1.4 ml) and the mixture was stirred for 2 hours at -78 C. and then stirred for 15 hours at 0 C. The reaction mixture was diluted with ethyl acetate and then washed with 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1?3:2) to give the title compound (1.70 g) having the following physical data. TLC: Rf 0.50(Methylene chloride:Methanol=19:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; | 1 General synthesis of intermediate d: To a flask charged with D- or L-phenylglycinol (1.0 eq) and benzo[b]thiophene-2-carbonyl chloride (1.2 eq) was added anhydrous tetrahydrofuran and diisopropylethyl amine (2.5 eq). The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was diluted in ethyl acetate and washed with 2 X 0.5M HCl (aqueous) then 3 X brine. The organic layer was dried with sodium sulfate and concentrated to dryness. The resultant residue was purified by flash column chromatography (silica gel 0-20% methanol in dichloromethane). |
With triethylamine In chloroform at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; at 115℃; for 12h;Sealed tube; | General procedure: [60] In a sealed tube, a mixture of 1 [61] (2.74 g,10 mmol) and (R or S)-phenylglycinol (3.43 g, 25 mmol) in methanol (10 mL) was stirred at 115 C for 12 h. After cooling toroom temperature, the crude product was poured into ice water(100 mL), stirred for 15 min, filtered, washed with water(20 mL 3) and the residues was dried under vacuum. The whiteproduct was used for the next step without further purification (4.41 g, 91%). 1H NMR (400 MHz, CDCl3): d 8.60 (d, J 7.6 Hz, 2 H),8.45 (s, 2 H), 7.37-7.29 (m, 10 H), 5.26-5.22 (m, 2 H), 4.01 (d,J 4.4 Hz, 4 H), 2.21 (br, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With N-ethyl-N,N-diisopropylamine; at 130℃; for 60h; | Example 5a Preparation of (R)-N-(6-chloroquinolinyl-2)-2-Hydroxy-1-phenylethylamine (1e) A 15-mL pressure tube charged with <strong>[1810-72-6]2,6-dichloroquinoline</strong> (1.352 g, 6.83 mmol), (R)-phenylglycinol (0.964 g, 7.03 mmol), N,N-diisopropylethylamine (0.991 g, 7.67 mmol) and a stir bar was flushed with nitrogen several times, stoppered and heated at 130+-5 C for 2.5 days. The tube was allowed to cool to room temperature and the content was diluted with CH2Cl2. DIPEAHCl precipitated out. The mixture was washed with saturated aqueous NH4Cl to remove DIPEA and then with saturated aqueous NaHCO3. The solution was dried over Na2SO4 and evaporated to afford 1.770 g of the crystalline product (87%), which was sufficiently pure for the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With N-ethyl-N,N-diisopropylamine; 1,2-dichloro-benzene; In toluene; at 195℃; for 24h;Dean-Stark; | A 250 mL round-bottomed flask containing a stirrer bar was chargedwith (R)-2-phenylglycinol [(R)-2; 10.00 g, 72.80 mmol, 1.05 equiv), odichlorobenzene(34.5 mL, 2.0 M), i-Pr2NEt (31.0 mL, 173.6 mmol, 2.5equiv), and <strong>[615-20-3]2-chlorobenzothiazole</strong> (1; 8.60 mL, 69.43 mmol, 1.0equiv). The resulting yellow suspension was stirred vigorously andheated to reflux at 195 C (DrySyn temperature), at which point thesuspended solid had dissolved to leave a yellow solution. After 24 h atreflux,24 the orange reaction mixture was allowed to cool to r.t. Oncecooled, the mixture was diluted with distilled H2O (100 mL) and toluene(75 mL) with vigorous stirring. A precipitate formed over the next15 min and stirring was maintained for a further 1 h. The reactionmixture was filtered through a 1.0 L sintered glass filter funnel (porosity3) under vacuum to leave the solid precipitate. The solid waswashed with toluene (2 × 100 mL) and dried on the sinter under vacuumfor 30 min until a free-flowing powder was obtained. The crudeproduct (typically 22-24 g) was transferred to a 500 mL round-bottomedflask containing a stirrer bar, followed by toluene (100 mL). A10 mL Dean-Stark trap filled with toluene and a reflux condenserwere fitted to the flask, and the suspension heated to reflux (180 CDrySyn temperature). Once at reflux, further 10 mL portions of toluenewere added down the condenser, waiting ~5 min between portions,until a clear solution was obtained (4-6 portions were typicallyneeded). The reflux was maintained until no further H2O was observedcondensing into the trap (typically 30 min were sufficient).The flask was removed from the heating block and allowed to coolslowly to r.t., over which time a precipitate formed. Once cooled, theflask was further cooled to -10 C in a NaCl/ice/water bath for 30 min.The solid precipitate was recovered by vacuum filtration on a 1.0 Lsintered glass filter funnel (porosity 3), and washed with further portionsof toluene (2 × 100 mL). The solid was dried on the sinter undervacuum for 30 min, then transferred to a 250 mL round-bottomedflask and dried in vacuo to constant weight. This gave title compound(R)-3 as fluffy white crystals; yield: 14.81 g (54.78 mmol, 79%). A secondrecrystallisation from toluene at reflux may be required if a powderis obtained from the first attempt. Typical mass loss on secondrecrystallisation was 99% ee.1H NMR (500 MHz, MeOH-d4): delta = 3.80 [1 H, dd, J = 11.4, 7.4 Hz,C(1)HAHB], 3.85 [1 H, dd, J 11.4, 5.0 Hz, C(1)HAHB], 5.00 [1 H, dd, J = 7.4,5.0 Hz, C(2)H], 7.03 (1 H, td, J = 7.5, 1.1 Hz, ArH), 7.22 (1 H, td, J = 7.5,1.2 Hz, ArH), 7.26 (1 H, t, J = 7.4 Hz, p-PhH), 7.34 (2 H, t, J = 7.4 Hz, m-PhH), 7.38 (1 H, d, J = 8.1 Hz, ArH), 7.44 (2 H, d, J = 7.4 Hz, o-PhH), 7.55(1 H, d, J = 7.8 Hz, ArH).13C{1H} NMR (126 MHz, MeOH-d4): delta = 62.2, 66.9, 119.0, 121.7, 122.7,126.8, 128.1, 128.6, 129.5, 131.3, 141.1, 153.0, 169.0.Anal. Calcd for C15H14N2OS: C, 66.64; H, 5.22; N, 10.36. Found: C,66.57; H, 5.31; N, 10.33.1H and 13C NMR data were consistent with literature values.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16h; | D-phenylglycinol (compound 34, 1.03 g, 7.5 mmol) was coupled with <strong>[1001413-01-9]1-(3,4-difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid</strong> (compound 35, 1.59 g, 6 mmol, Compound 20.2), using 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydride (1.15 g, 6 mmol) and 1-hydroxybenzotriazole hydrate (0.92 g, 6 mmol) as coupling agent, and N,N-diisopropylethylamine (3.15 ml, 18 mmol) as base in 10 ml DMF at room temperature overnight. Then the solvent was removed under vacuum and the residue was flooded with ethyl acetate, rinsed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered, and evaporated to dryness. This was purified using flash chromatography to give compound 36 (1.94 g, 84%) as brown oil. ES (+) MS m/e = 385 (M+1). 1H NMR (400 MHz, DMSO-d6) ? ppm 3.65 (m, 2 H) 5.01 (m, 2 H) 5.23 (m, 2 H) 6.57 (t, J=6.85 Hz, 1 H) 7.20 (m, 2 H) 7.30 (m, 4 H) 7.45 (m, 2 H) 8.21 (dd, J=6.85, 2.45 Hz, 1 H) 8.32 (dd, J=7.34, 1.96 Hz, 1 H) 10.26 (d, J=7.83 Hz, 1 H). |
84% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; | D-phenylglycinol (1.03 g, 7.5 ?tmol) was coupled with l-(3,4-difluoro-benzyl)-2- oxo-1, 2-dihydro-pyridine-3-carboxylic acid (1.59 g, 6 mmol, Compound 20.2), using l-(3- Dimethylaminopropyl)-3-ethylcarbodiiraide hydride (1.15 g, 6 mmol) and 1- hydroxybenzotriazole hydrate (0.92 g, 6 mmol) as coupling agent, and N5N- diisopropylethylamine (3.15 ml, 18 mmol) as base in 10 ml DMF at room temperature overnight. Then the solvent was removed under vacuum and the residue was flooded with ethyl acetate, rinsed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered, and evaporated to dryness. This was purified using flash chromatography to give Compound 55.1 (1.94 g, 84%) as brown oil. ES (+) MS m/e = 385 (M+l). 1H NMR (400 MHz, DMSO-?6) ppm 3.65 (m, 2 H) 5.01 (m, 2 H) 5.23 (m, 2 H) 6.57 (t, J=6.85 Hz, 1 H) 7.20 (m, 2 H) 7.30 (m, 4 H) 7.45 (m, 2 H) 8.21 (dd, J=6.85, 2.45 Hz, 1 H) 8.32 (dd, j=7.34, 1.96 Hz, 1 H) 10.26 (d, ./=7.83 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane; at 25 - 90℃; | Example 8Preparation of the (R)-(-)-phenylglycinol salt of (R)-(-)-3-(carbamoylmethyl)-5- methylhexanoic acid in 1 ,4-dioxane.8 g (42.8 mmoles) of <strong>[181289-15-6]3-(carbamoylmethyl)-5-methylhexanoic acid</strong> racemate are added to 30 ml of 1,4-dioxane at 25C. The suspension is heated at 70C in order to obtain complete dissolution. Separately, a solution of 4 g (29.2 mmoles) of (R)-(-)- phenylglycinol in 50 ml of 1,4-dioxane is prepared at 70C, which is then added dropwise to the reaction flask over approx. 10 minutes, while maintaining the temperature at 70-750C. The mixture is heated at 900C until complete solution is obtained. The mixture is cooled slowly to 7O0C to obtain the crystallisation of the salt. The solid is filtered at 65-7O0C and washed with 10 ml of 1,4-dioxane. The wet product is dried at 400C for 6 hours giving 4.4 g of the (R)-(-)-phenylglycinol salt of (R)-(-)-<strong>[181289-15-6]3-(carbamoylmethyl)-5-methylhexanoic acid</strong> as a white solid with a melting point between 158 and 161C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
toluene-4-sulfonic acid; In xylene; for 48h;Heating / reflux; | 4- (5-METHYL- [1, 3,4] OXADIAZOL-2-YL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ester (1 g, 3.7 MMOL) (see reference WO 0039125), (R)- (-)-2-AMINO-2-PHENYLETHANOL (617 mg, 4.4 MMOL) and 4-methylphenylsulphonic acid (20 mg) in Xylene (10 ml) were heated under reflux for 48 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between DICHLOROMETHANE and sodium hydrogen carbonate solution. The aqueous layer was extracted with DICHLOROMETHANE and the combined organic layers were washed with brine, dried over magnesium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using methanol and ammonium hydroxide in DICHLOROMETHANE as eluant (10: 1: 90). The material obtained was dissolved in 4M hydrogen chloride solution in 1,4-dioxane and the mixture was stirred at 15C for 2 hours. The solvent was evaporated under reduced pressure and the residue was triturated with diethyl ether. The material obtained was mixed with 2-bromopyrimidine (170 mg, 1.1 MMOL) and potassium carbonate (308 mg, 2.2 MMOL) in N, N-dimethylformamide (1 ml) and was heated at 50C for 4 hours. The reaction mixture was cooled to room temperature and was partitioned between water and dichloromethane. The aqueous phase was extracted with DICHLOROMETHANE and the combined organic phases were washed with brine, dried over magnesium sulphate and evaporated under reduced pressure. The residue was pre- adsorbed onto a small quantity of silica gel and then was purified by chromatography on silica gel using methanol and ammonium hydroxide in ethyl acetate as eluant (9: 0.1 : 91) to give the title compound as a white solid (46 mg). 'H NMR (400MHZ, CECI3) : o 1.75 (m, 1H), 1.83 (m, 3H), 2.15 (s, 3H), 2.70 (t, 1H), 2.84 (m, 2H), 4.01 (t, 1H), 4.40 (m, 1H), 4.70 (m, 2H), 5.12 (s, 1H), 5.42 (m, 1 H), 6.38 (d, 1 H), 7.06 (d, 2H), 7.29 (m, 3H), 8.20 (d, 2H). LCMS: M/Z ES+ 365 [M+NA] + |
Yield | Reaction Conditions | Operation in experiment |
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With P2O5; triethylamine; In pyridine; ethanol; dichloromethane; | Preparation 1 2-(3-(S)-Methoxymethoxypyrrolidin-1-yl)-2-(R)-phenylethanol To a stirred solution of (S)-(-)-1,2,4-butanetriol (10.61 g, 0.1 mol) in pyridine (50 ml) was added p-toluenesulfonyl chloride (38.13 g, 0.2 mol) by portions at 0 C. After 14 h stirring, the reaction mixture was poured into conc. HCl aqueous solution including ice and acidified to pH2. The mixture was extracted with ether (100 ml*3). The extract combined was washed with brine, dried (Na2SO4), and concentrated to give 18.58 g of colorless oil. To a stirred solution of this crude ditosylate (18.58 g, 45.7 mmol) and dimethoxymethane (50 ml) in CH2Cl2 (50 ml) was added P2O5 by portions at rt (room temperature) and stirred for 26 h. The CH2Cl2 layer was separated and the P2O5 (50 g) solid was washed with CH2Cl2 (50 ml*4). The CH2Cl2 layer combined was washed with saturated NaHCO3 aqueous solution and brine. After dry (Na2SO4), the solvent was evaporated to afford 18.01 g of brown viscous oil. A mixture of this oil (18.00 g,40 mmol), R-(-)-2-phenylglycinol (4.80 g, 35 mmol), and Et3N (11.3 ml, 80 mmol) in ethanol (20 ml) was refluxed with stirring for 8 h. The solvent was evaporated and the residue was dissolved in CH2Cl2 (200 ml). This solution was washed with saturated NaHCO3 aqueous solution and brine, dried (Na2SO4), and concentrated to give 16.69 g of brown viscous oil, which was purified by column chromatography (silica gel 200 g, CH2Cl2/MeOH: 20/1) to afford 5.13 g (20.4%, over all yield) of clear brown viscous oil. 1H NMR (270 MHz, CDCl3) delta 7.40-7.25 (5H, m), 4.62 (1H, d, J=7.0 Hz), 4.58(1H, d, J=7.0 Hz), 4.25-4.15 (1H, m), 3.88 (1H, dd, J=5.9, 10.6 Hz), 3.80 (1H, dd, J=5.9, 10.6 Hz), 3.50 (1H, t, J=5.9 Hz), 3.33 (3H, s), 2.76 (1H, dt, J=6.2, 8.4 Hz), 2.71 (1H, dd, J=5.9, 10.3 Hz), 2.63 (1H, dd, J=3.3, 10.3 Hz), 2.45 (1H, dt, J=6.2, 8.1 Hz), 2.18 (1H, br. s), 2.16-2.02 (1H, m), 1.87-1.75 (1H, m). IR(neat): 3450 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In isopropyl alcohol; at 0℃; for 9h;Reflux; | General procedure: Compounds 2-5 were synthesized using a modified procedure originally reported by Roehrig et al.28 To a cooled solution of <strong>[181140-34-1](R)-(-)-N-(2,3-epoxypropyl)phthalimide</strong> 1 (102 mg, 0.50 mmol) in 10 mL of 2-propanol, amine or aminoalcohol (0.6 mmol, 1.2 equiv) in 10 mL of 2-propanol was added at 0 C and stirred for 1 h. It was then refluxed for 8 h. After the completion of the reaction, the solvent was removed under reduced pressure and the crude product was purified by flash chromatography on silica gel (CHCl3/MeOH 1:20 as eluent) to afford 2-5 as white crystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | General procedure: Constant current electrolyses (I = 25 mA cm-2) were performed under a nitrogen atmosphere, at 20C, using an Amel Model 552 potentiostat equipped with an AmelModel 731 integrator. All the experiments were carried out in a divided glass cell separated through a porous glass plug filled up with a layer of gel (i.e., methylcellulose 0.5% vol dissolved in DMF-Et4NPF6 1.0 mol dm-3); Pt spirals (apparent areas 0.8 cm2) were used both as cathode and anode. MeCN-Et4NPF6 0.1 mol dm-3 was used as solvent-supporting electrolyte system (catholite: 20 cm3; anolite: 5 cm3).1 mmol of substrate was present in the catholyte (except for D-cycloserine, which was added to the catholyte after the end of the electrolysis). After 145 C (if not otherwise stated) were passed, the current was switched off and 1 mmol of alkylating agent was added to the catholyte. The solution was kept under stirring at room temperature for 2 hours, than the solvent was evaporated under reduced pressure and the residue was extracted three times with diethyl ether. The products were purified by flash column chromatography, using a mixture of ethyl acetate/light petroleum ether 2/8 in volume. The reactions on D-cycloserine were carried out following the general method, but the substrate was added to the catholyte after the end of the electrolysis. After 15 minutes at room temperature, the alkylating agent was added and the solution was kept under stirring at rt for 2 hours. The solvent was evaporated under reduced pressure and the residue was treated with 1 cm3 of saturated acqueous NaHCO3 and 1 mmol of ethyl chloroformate, at 0C, for 2 h. The solution was then acidified with diluted HCl (pH 4) and extracted with diethyl ether. The products were purified by flash column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
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82% | In butan-1-ol; at 145℃; for 24h; | General procedure: Compound 1 (1.00 g, 4.01 mmol) was mixed with the benzylamine (12.03 mmol) and 1-butanol (3.5 mL) and agitated at 145 C for 18-24 h. Then the mixture was cooled to rt, diluted with water (50 mL) and diethyl ether (150 mL) or EtOAc (150 mL). After phase separation, the water phase was extracted with more diethyl ether (2 × 50 mL) or EtOAc (2 × 50 mL). The combined organic phases were washed with saturated aq NaCl solution (50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo, before the crude oil was dried under reduced pressure to constant weight to remove excess benzylamine. The compounds were purified by silica-gel column chromatography or crystallized as specified for each individual compound |
Yield | Reaction Conditions | Operation in experiment |
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87% | 2,2-Dimethyl-4-pentenoic acid (128 mg, 1.0 mmol) was added to a flame-dried flask with stir bar and sealed under nitrogen. Dry DCM (5.0 mL) was added, then the flask was cooled on ice and oxalyl chloride (0.092 ml, 1.05 mmol) was added, followed by DMF (1 drop from a 22-gauge needle). The reaction was removed from the ice bath and stirred for 20 h, then (i-Pr)2NEt (0.437 ml, 2.50 mmol) was added, followed by (R)-2-phenylglycinol (206 mg, 1.50 mmol). The reaction was stirred for another 20 h, then it was diluted with EtOAc and 1 M aq. HCl. The layers were separated, and the combined organics were washed again with aq. HCl, then twice with half-saturated aq. NaHCO3, then brine. The organic phase was dried over MgSO4, filtered, and concentrated to give the desired product as a white solid (214 mg, 87%). LRMS (ESI+) (M+H): 248.20. |
Yield | Reaction Conditions | Operation in experiment |
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1 g | With copper(l) iodide; potassium carbonate; L-proline; In dimethyl sulfoxide; at 100℃; for 12h;Inert atmosphere; | Step 1: Preparation of (/f)-2-(5-bromo-6-methyl-pyridin-3-ylamino)-2-phenyl-ethanol Chiral Under an Ar atmosphere, a mixture of <strong>[38749-87-0]3,5-dibromo-2-methyl-pyridine</strong> (2 g, 8 mmol), D-(- )-alpha-phenylglycinol (1.32 g, 9.6 mmol), copper(I) iodide (0.15 g, 0.8 mmol), L-proline (0.184 g, 1.6 mmol) and potassium carbonate (2.2 g, 16 mmol) in DMSO (30 mL) was heated at 100 C for 12 hours. The mixture was diluted with water and filtered to remove the catalyst. The aqueous layer was extracted with EtOAc. The organic layer was washed with brine, and then dried over Na2S04 and concentrated. The residue was purified by chromatography column to give (/?)-2-(5-bromo-6-methyl-pyridin-3-ylamino)-2-phenyl-ethanol (1 g). |
Yield | Reaction Conditions | Operation in experiment |
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General procedure: A solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids. |
Yield | Reaction Conditions | Operation in experiment |
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46% | With tetrachloromethane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In dichloromethane; at 0 - 20℃; for 12h;Inert atmosphere; | Take 500mL dry reaction bottle,Argon protection,Intermediate R-4a (4.0 g, 12 mmol) was added to the reaction flask,Triphenylphosphine (9.3 g, 36 mmol)D-phenylglycinol 5a (1.6 g, 12 mmol) andAnhydrous dichloromethane (50 mL),Ice bath until fully dissolved,Diisopropylethylamine (6.2 mL, 36 mmol) was added,Take carbon tetrachloride (6.0 mL, 60 mmol) andAnhydrous dichloromethane (50 mL) into a dropping funnel,Drop slowly into the reaction bottle, 3h drop finished,Gradually return to room temperature and stir overnight.After completion of the reaction, the reaction was dry under reduced pressure, ethyl acetate was added and allowed to stand for 1 hour.The white solid was removed by filtration and the solution was dry under reduced pressure.The white solid intermediate R-6a (2.3 g, 46%) was obtained by column chromatography with ethyl acetate: petroleum ether = 1: 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 105℃; for 20h;Inert atmosphere; | To a stirred solution of (R)-2-amino-2-phenylethanol (500 mg, 3.64 mmol) in N,N- dimethylformamide (8.0 mL) under an atmosphere of nitrogen was added N,N-diisopropyl-N- ethylamine (9.0 mL, 49 mmol) followed by <strong>[3939-12-6]6-fluoronicotinonitrile</strong> (445 mg, 3.64 mmol). The resulting mixture was heated at 105 °C for 20 h, cooled to ambient temperature, diluted with ethyl acetate (40 mL) and washed with water (10 mL x 3). The ethyl acetate layer was washed with brine (5 mL), dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo. The crude residue was purified by flash silica gel chromatography (ISCO CombiFlash Rf Purification System®; 40 g SepaFlash® Silica Flash Column, eluting with a 0-100percent ethyl acetate in hexanes gradient) to afford the title compound as a foam. MS (ESI) m/z [M+H]+: 240.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82%; 10% | In ethanol; at 100℃; for 24h;Inert atmosphere; Sealed tube; | General procedure: To the mixture of vicinal amino alcohol (1, 1.0 mmol, 1.0 equiv.) in absolute ethanol (2.0 mmol),potassium ethylxanthate (5.0 mmol, 5.0 equiv.) was added quickly. After flushed with N2 for 5 mins,the suspension was sealed and heated in an oil bath at 100 C for 24 hr. The it was cooled down toroom temperature, the mixture was transferred to a 50 mL-round bottom flask, and evaporated underreduced pressure to remove alcohol. Then water (10 mL) was added to the slurry and extracted withethyl acetate (30 mL*3). Combined organic phase was washed with brine (30 mL) and dried overanhydrous Na2SO4. After concentration, the crude product was obtained. Then it was applied onsilica gel for flash chromatography to afford corresponding 1,3-thiazolidine-2-thione (2). For somecases, 1,3-oxazolidine-2-thione (3) was obtained as side product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of <strong>[393-15-7]4-methoxy-3-(trifluoromethyl)aniline</strong> (aniline), (1.00 eq) in dichloromethane (3 ml) is added triphosgene (0.35 eq) at 0 C. Then saturated sodium bicarbonate (3 mL) is added dropwise to the mixture at 0 C. After stirred for 1 h, the mixture is allowed to stand for 5 min. The organic layer is separated, dried over anhydrous sodium sulfate and filtered. (R)-2-amino-2-phenylethan-1-ol (amine) (1.00 eq) is added into organic layer at 0 C. The mixture is stirred at 0-25 C for another 4 h. After removal of solvent, the residue is purified by prep-HPLC and lyophilized to give target molecule. |
Tags: 56613-80-0 synthesis path| 56613-80-0 SDS| 56613-80-0 COA| 56613-80-0 purity| 56613-80-0 application| 56613-80-0 NMR| 56613-80-0 COA| 56613-80-0 structure
[ 1256974-17-0 ]
(S)-2-Amino-2-(p-tolyl)ethanol hydrochloride
Similarity: 0.97
[ 1810074-71-5 ]
(S)-2-(Methylamino)-2-phenylethanol hydrochloride
Similarity: 0.85
[ 1245623-77-1 ]
(R)-3-(1-Amino-2-hydroxyethyl)benzonitrile hydrochloride
Similarity: 0.81
[ 146812-68-2 ]
3-(1-Amino-2-hydroxyethyl)phenol hydrochloride
Similarity: 0.81
[ 1391355-45-5 ]
(R)-4-(1-Amino-2-hydroxyethyl)phenol hydrochloride
Similarity: 0.81
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