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[ CAS No. 2749-11-3 ] {[proInfo.proName]}

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Chemical Structure| 2749-11-3
Chemical Structure| 2749-11-3
Structure of 2749-11-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2749-11-3 ]

CAS No. :2749-11-3 MDL No. :MFCD00064412
Formula : C3H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :BKMMTJMQCTUHRP-VKHMYHEASA-N
M.W : 75.11 Pubchem ID :80307
Synonyms :
(S)-2-Amino-1-propanol;(S)-2-Aminopropanol;2-Aminopropanol;(S)-Alaninol

Calculated chemistry of [ 2749-11-3 ]

Physicochemical Properties

Num. heavy atoms : 5
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 20.4
TPSA : 46.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.45 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.92
Log Po/w (XLOGP3) : -0.97
Log Po/w (WLOGP) : -0.67
Log Po/w (MLOGP) : -0.63
Log Po/w (SILICOS-IT) : -0.78
Consensus Log Po/w : -0.43

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.37
Solubility : 177.0 mg/ml ; 2.35 mol/l
Class : Highly soluble
Log S (Ali) : 0.48
Solubility : 229.0 mg/ml ; 3.05 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.34
Solubility : 166.0 mg/ml ; 2.21 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 2749-11-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:2735
Hazard Statements:H227-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2749-11-3 ]

* 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.

  • Upstream synthesis route of [ 2749-11-3 ]
  • Downstream synthetic route of [ 2749-11-3 ]

[ 2749-11-3 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 6168-72-5 ]
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  • [ 35320-23-1 ]
Reference: [1] Patent: WO2010/148191, 2010, A2, . Location in patent: Page/Page column 45-49; 59
[2] Chemical Communications, 2015, vol. 51, # 43, p. 8931 - 8934
  • 2
  • [ 56-41-7 ]
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  • [ 35320-23-1 ]
Reference: [1] Organic Letters, 2003, vol. 5, # 4, p. 527 - 530
  • 3
  • [ 6168-72-5 ]
  • [ 72-19-5 ]
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  • [ 35320-23-1 ]
  • [ 1492-24-6 ]
  • [ 116-09-6 ]
Reference: [1] Green Chemistry, 2012, vol. 14, # 8, p. 2137 - 2140
  • 4
  • [ 50-00-0 ]
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  • [ 2812-31-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1975, vol. 18, p. 292 - 300
  • 5
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  • [ 100-52-7 ]
  • [ 6940-80-3 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With magnesium sulfate In dichloromethane at 25℃; for 19 h;
Stage #2: With sodium tetrahydroborate In methanol at 0 - 25℃; for 18 h;
Step 1: (S)-Alininol (17.5 g, 233 mmol), PhCHO (26 g), and MgSO4 (70 g) were taken up in DCM and stirred at 25 0C for 19 h. The solution was filtered and concentrated which furnished a yellow solid. The residue was taken up in MeOH and cooled to O 0C. Sodium borohydride (11 g, 288 mmol) was added in portions to the solution at 0 0C (gas evolution). After the addition, the solution was stirred at 25 0C for 18 h. The solution was concentrated, and the residue was quenched carefully with 3 M HCI (aq.) (gas evolution/exotherm). The aqueous acidic layer was extracted with Et2O (4 X 200 ml_). The aqueous layer was cooled to 0 0C and made basic via addition of NaOH pellets (pH = 11 -12). The aqueous layer was extracted with DCM. The combined DCM layers were dried (MgSO4). Filtration and concentration gave 23.2 g (60percent) of the amino-alcohol as a white solid.
Reference: [1] Tetrahedron, 1996, vol. 52, # 48, p. 15157 - 15170
[2] Synthetic Communications, 1994, vol. 24, # 10, p. 1415 - 1424
[3] Patent: WO2009/5646, 2009, A2, . Location in patent: Page/Page column 219-220
[4] Tetrahedron Letters, 1995, vol. 36, # 46, p. 8391 - 8394
[5] Patent: US2006/14948, 2006, A1, . Location in patent: Page/Page column 11
[6] Patent: US2011/136778, 2011, A1, . Location in patent: Page/Page column 47-48
[7] MedChemComm, 2013, vol. 4, # 2, p. 394 - 405
[8] Journal of Organic Chemistry, 2016, vol. 81, # 24, p. 12075 - 12083
  • 6
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  • [ 7321-55-3 ]
  • [ 112245-13-3 ]
  • [ 181708-51-0 ]
  • [ 131833-93-7 ]
Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 15, p. 2270 - 2275
  • 7
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  • [ 141-78-6 ]
  • [ 94695-48-4 ]
  • [ 109-94-4 ]
  • [ 106939-34-8 ]
YieldReaction ConditionsOperation in experiment
99.4%
Stage #1: With sodium hydride In toluene
Stage #2: at 20℃; Reflux
Stage #3: With potassium fluoride In N,N-dimethyl-formamideReflux
step 1, 2.6 g of sodium hydride, 50 ml of toluene and 8.8 g of ethyl acetate were sequentially placed in the reaction flask.Stir until it is gray and turbid.Then, 8.8 g of ethyl formate was slowly added dropwise, and stirring was continued while the bubbles were released.After the reaction was completed, it was filtered under reduced pressure, and the cake was dried in vacuo.Obtaining white formyl ethyl acetate sodium salt; Step 2. Add to the flask containing 50 ml of tolueneSodium formylacetate sodium salt 5.5gAnd ZIF-67ZnCoZIF catalyst 1.5g,Slowly add 7.7 g of 2,3,4,5-tetrafluorobenzoyl chloride at room temperature.After the reaction is completed, slowly add S-(+)-2-aminopropanol dropwise3.2g, heated to reflux,After the reaction is completed, a water layer is added, the water layer is extracted with toluene, the organic layers are combined, and toluene is distilled off to obtain a preliminary product; Step 3.The obtained initial product was slowly added dropwise to 30 ml of a DMF solution containing 5.8 g of KF, stirred, heated to reflux, and azeotropically dehydrated.After completion of the reaction, the solvent was evaporated, and washed with water to give a brown-yellow viscous solid.Drying to get the intermediate(S)-(-)-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7-hydropyrido[1,2,3-de][1,4 ] Benzoxazine-6-carboxylic acid ethyl ester.
Reference: [1] Patent: CN108440562, 2018, A, . Location in patent: Paragraph 0008; 0010-0015; 0016-0018; 0029
  • 8
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  • [ 124-38-9 ]
  • [ 4042-35-7 ]
YieldReaction ConditionsOperation in experiment
36% With caesium carbonate In dimethylsulfoxide-d6 at 25 - 150℃; for 24 h; 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 μL, 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).
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 35, p. 4717 - 4720
[2] RSC Advances, 2014, vol. 4, # 92, p. 50851 - 50857
  • 9
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Reference: [1] Patent: WO2018/11160, 2018, A1, . Location in patent: Page/Page column 43
  • 10
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  • [ 105-58-8 ]
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Reference: [1] Journal of the American Chemical Society, 1989, vol. 111, # 6, p. 2211 - 2217
[2] Journal of Molecular Catalysis A: Chemical, 2011, vol. 338, # 1-2, p. 33 - 43
  • 11
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Reference: [1] Chemistry Letters, 2013, vol. 42, # 2, p. 109 - 111
  • 12
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  • [ 616-38-6 ]
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Reference: [1] Tetrahedron, 2010, vol. 66, # 13, p. 2439 - 2443
  • 13
  • [ 2749-11-3 ]
  • [ 28920-43-6 ]
  • [ 161529-13-1 ]
YieldReaction ConditionsOperation in experiment
90% With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; To a mixture of (S)-2-aminopropan-l-ol (2 g, 26.6 mmol) and Na2C03 (5.6 g, 53.2 mmol) in 1,4-dioxane and water (25 mL / 25 mL) at 0 °C was added FmocCl (10.2 g, 39.9 mmol) and the resulting mixture was then warmed to room temperature gradually. After the amine was consumed completely as indicated by TLC, water (25 mL) was added. The mixture was extracted with DCM (3 x 50 mL). The organic phase was washed with brine (50 mL), and dried over anhydrous Na2S04. After filtration and concentration, the crude product was purified by column chromatography to give the title compound (7.1 g, 90percent).
Reference: [1] Patent: WO2011/69063, 2011, A2, . Location in patent: Page/Page column 82
  • 14
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  • [ 82911-69-1 ]
  • [ 161529-13-1 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydrogencarbonate; sodium carbonate In water; acetone General procedure: Suitable N-protected amino alcohols (e.g. Fmoc and boc) can be obtained by reacting an amino alcohol with a desired protecting group precursor that protects the amine group with the desired protecting group Pgi . For example, N-Fmoc protected amino alcohols were prepared (in an Erlenmeyer flask) by suspending/dissolving Fmoc-O-Su in acetone (in a ratio of about 2.5-6 mL acetone per mmol of Fmoc-O-Su) with stirring. To this briskly stirring solution was added dropwise a solution of the amino alcohol (in a ratio of about 1 to 1 .2 eq. per mmol of Fmoc-O-Su) dissolved in acetone (in a ratio of about 0.4- 1 .2 mL acetone per mmol of the amino alcohol) and occasionally some water if the amino alcohol is not completely soluble in the acetone alone. When addition was complete, a solution containing NaHC03 and Na2C03 (in a ratio of about 1 to 1 .1 mmol NaHC03 and 0.5 to 0.55 mmol Na2C03 per mmol of Fmoc-O-Su) dissolved in deionized water (in a ratio of about 1 mL deionized water per 1 mL of acetone originally added to the Fmoc-O-Su) was added dropwise to the stirring reaction. After stirring and analysis by TLC (indicating complete reaction), a solution containing enough HCI (dissolved in about 0.3 mL water per 1 mL of acetone originally added to the Fmoc-O-Su) to completely neutralize the NaHC03 and Na2C03 was added dropwise over 30 minutes to one hour. The pH of the solution was then adjusted to approximately 4-5 (pH paper) by addition of 1 N HCI. The flask was then heated on a hot plate stirrer until the solid dissolved. The solution was then allowed to cool overnight and the product crystallized. The crystalline product was then collected by vacuum filtration. The product was then optionally recrystallized (usually by a mixture of acetonitrile and water) to the desired level of purity.
Reference: [1] Tetrahedron, 1995, vol. 51, # 45, p. 12337 - 12350
[2] Patent: WO2018/175927, 2018, A2, . Location in patent: Paragraph 00307-00310
[3] Tetrahedron Letters, 1995, vol. 36, # 1, p. 167 - 168
  • 15
  • [ 2749-11-3 ]
  • [ 105-39-5 ]
  • [ 119844-66-5 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With sodium hydride In toluene at 0 - 20℃; for 0.5 h;
Stage #2: for 20 h; Heating / reflux
Stage #3: With ammonium chloride In toluene at 20℃; for 0.333333 h;
Step A: A solution of (S)-(+)-2-amino-1-propanol (5.0 g, 67.0 mmol) in toluene (60 mL) was added dropwise at 0° C. to a stirred suspension of NaH (60percent in mineral oil, 6.2 g, 145 mmol) in toluene (150 mL). The cooling bath was removed and the reaction mixture was stirred at room temperature for 30 min. A solution of ethyl chloroacetate (8.0 mL, 73.8 mmol) in toluene (60 mL) was then added dropwise at room temperature and the resulting reaction mixture heated at reflux for 20 h. The reaction was cooled to room temperature and solid NH4Cl (5 g, 96.7 mmol) added to the reaction. The reaction mixture was stirred for 20 min, filtered and the filtrate concentrated under reduced pressure. Purification by column chromatography (silica gel, 94.5:5:0.5 CH2Cl2/CH3OH/NH4OH) afforded (S)-5-methylmorpholine-3-one (6.5 g, 84percent) as an off-white semi-solid. 1H NMR and MS consistent.
Reference: [1] Patent: US2008/255114, 2008, A1, . Location in patent: Page/Page column 17
[2] Journal of Organic Chemistry, 1996, vol. 61, # 15, p. 4990 - 4998
  • 16
  • [ 2749-11-3 ]
  • [ 79-04-9 ]
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YieldReaction ConditionsOperation in experiment
9 g
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1 h; Inert atmosphere
In the reaction flask,L-aminopropanol (7.5 g, 0.1 mol) was added to DMF (30 mL)After completely dissolving,Sodium hydride (50 wtpercent) (5 g, 0.10 mol) was added thereto at 0 & lt; 0 & gt; C under nitrogen,Then rose to room temperature,After stirring for 1 h, chloroacetyl chloride (11 g, 0.1 mol) was added,Reaction overnightTLC monitoring raw material reaction is complete,Saturated sodium chloride solution (500 mL) was added to the reaction solution,And extracted twice with ethyl acetate (400 mL)Combine organic phase,To the organic phase slowly dropping dilute hydrochloric acid solution,Gradually solid precipitation,When the pH of the reaction solution was 11,The precipitation of solids to achieve the most,The filter solution was filtered and the cake was dried to give (S) -3 methyl morpholinone hydrochloride,(S) -3-methylmorpholinone hydrochloride was added to methanol (50 mL)And then slowly dropping dilute hydrochloric acid solution,Solid gradually dissolved,After being completely dissolved, the solvent methanol was distilled off, the reaction solution was extracted with ethyl acetate,The organic phases were combined and concentrated to give 9 g of pale yellow liquid (S) -3 methylmorpholinone.
Reference: [1] Patent: CN106749081, 2017, A, . Location in patent: Paragraph 0013; 0014; 0015
  • 17
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  • [ 542-58-5 ]
  • [ 119844-66-5 ]
YieldReaction ConditionsOperation in experiment
17%
Stage #1: With sodium hydride In tetrahydrofuran for 0.583333 h;
Stage #2: for 3.5 h; Heating / reflux
[Example 105] (+)(3S)-4-[1-(6-Methoxypyridazin-3-yl)-5-(2-pyridyl)-1H-pyrazole-3-carbonyl]-3-methylmorpholine [Show Image] 1) (5S)-5-Methyl-3-morpholinone Sodium hydride (55percent, 0.409 g) was added to a solution of (2S)-2-amino-1-propanol (0.665 mL) in tetrahydrofuran (100 mL), and the resultant mixture was stirred for 35 minutes. Chloroethyl acetate (0.900 mL) was added to the reaction solution, and the mixture was stirred for 30 minutes, and then heated to reflux for 3 hours. After air cooling, the reaction solution was filtered, and a residue obtained by evaporating the solvent of the filtrate under reduced pressure was purified by silica gel column chromatography (ethyl acetate-n-hexane), to obtain a crude product of (5S)-5-methyl-3-morpholinone (0.170 g, 17percent) as an amorphous material.
Reference: [1] Patent: EP1785418, 2007, A1, . Location in patent: Page/Page column 147-148
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  • [ 98-74-8 ]
  • [ 374783-78-5 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 9, p. 3566 - 3569
[2] Tetrahedron, 2001, vol. 57, # 36, p. 7665 - 7674
  • 19
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  • [ 1335210-23-5 ]
  • [ 1335210-24-6 ]
Reference: [1] Patent: WO2011/119566, 2011, A1, . Location in patent: Page/Page column 9
  • 20
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  • [ 1335210-24-6 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 3, p. 564 - 567
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  • [ 1335210-24-6 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 3, p. 564 - 567
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  • [ 1335210-24-6 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 3, p. 564 - 567
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