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[ CAS No. 61477-40-5 ] {[proInfo.proName]}

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Chemical Structure| 61477-40-5
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Product Details of [ 61477-40-5 ]

CAS No. :61477-40-5 MDL No. :MFCD13184351
Formula : C4H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :AGMZSYQMSHMXLT-SCSAIBSYSA-N
M.W : 89.14 Pubchem ID :9898801
Synonyms :

Calculated chemistry of [ 61477-40-5 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 25.21
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) : -7.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.22
Log Po/w (XLOGP3) : -0.61
Log Po/w (WLOGP) : -0.28
Log Po/w (MLOGP) : -0.18
Log Po/w (SILICOS-IT) : -0.43
Consensus Log Po/w : -0.06

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.12
Solubility : 118.0 mg/ml ; 1.33 mol/l
Class : Highly soluble
Log S (Ali) : 0.11
Solubility : 115.0 mg/ml ; 1.29 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.09
Solubility : 72.1 mg/ml ; 0.809 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 61477-40-5 ]

Signal Word:Danger Class:8,3
Precautionary Statements:P210-P280-P370+P378-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310 UN#:2734
Hazard Statements:H314-H226 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 61477-40-5 ]

* 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 [ 61477-40-5 ]
  • Downstream synthetic route of [ 61477-40-5 ]

[ 61477-40-5 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 5303-65-1 ]
  • [ 61477-39-2 ]
  • [ 61477-40-5 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 20, p. 2895 - 2898
  • 2
  • [ 1236049-43-6 ]
  • [ 61477-40-5 ]
YieldReaction ConditionsOperation in experiment
91% With triethanolamine; sodium methylate In methanol at 80 - 100℃; 1.2 Release of (R)-3-amino-1-butanol From the (S)-mandelic Salt Thereof; The (S)-mandelic salt of (R)-3-amino-1-butanol obtained in Example 1.1 (372 g, 1.54 mol) was suspended in triethanolamine (1 I) at 80° C., and the slurry was admixed with sodium methoxide (277.6 g, 1.54 mol; 30percent in methanol), which gave a clear solution. This was heated to 100° C. and vacuum was applied. In a stepwise manner, a pressure of 750, 500, 250, 100, 50 and finally 20 mbar was applied. Through an attached Claisen distillation head (no return stream, no column), a clear distillate distilled over at a top temperature of 50 to 60° C., which was predominantly methanol. The pressure was then lowered further to 5 mbar, and (R)-3-amino-1-butanol distilled over at a top temperature of 76° C. The product was distilled once again in a water jet pump vacuum, in the course of which (R)-3-amino-1-butanol distilled over at 93° C. and 26 mbar. This gave 125 g (91percent of theory) of (R)-3-amino-1-butanol as a colorless liquid with an optical purity of 99.6percent ee.The optical purity of (R)-3-amino-1-butanol was determined by means of GC. To this end, (R)-3-amino-1-butanol (200 mg) and triethylamine (300 mg) were dissolved in diethyl ether (15 ml) and admixed with trifluoroacetic anhydride (0.6 ml). After stirring for 30 minutes, saturated ammonium chloride solution (5 ml) was added and the mixture was stirred for a further 15 minutes. Subsequently, the mixture was left to stand until two phases had formed, and a sample of the upper clear phase was analyzed by GC.Column: Hydrodex-TBDAc, 25 m.x.0.25 mm, Macherey NagelInlet temperature: 250° C.Detector temperature: 250° C.Injection volume : 0.5 μlMode: SplitSplit ratio: 100:1Carrier gas: HeFlow: 0.8 ml/min (constant flow)Program:Initial temperature: 135° C.Initial time: 10 minRate: 5° C./minFinal temperature: 170° C.Final time: 35 minRetention times:R enantiomer: 17.68 min (N-trifluoroacylated) 21.23 min (N,O-bis-trifluoroacylated)S enantiomer: 18.24 min (N-trifluoroacylated) 20.11 min (N,O-bis-trifluoroacylated)
35 g With sodium methylate In methanol at 20℃; for 2 h; The obtained product R-3-aminobutanol-S-mandelate was added into methanol (300 mL), and then a methanol solution (200 mL) dissolved with sodium methoxide (50 g) was slowly added and reacted at room temperature for 2 h, The reaction solution was concentrated, and further ethyl acetate (500 mL) was added. The reaction solution was filtered and the ethyl acetate was distilled off under reduced pressure to obtain the target product R-3-aminobutanol (35 g,0.393 mol).
Reference: [1] Patent: US2011/275855, 2011, A1, . Location in patent: Page/Page column 6-7
[2] Patent: CN106748816, 2017, A, . Location in patent: Paragraph 0033; 0035
  • 3
  • [ 167216-17-3 ]
  • [ 61477-40-5 ]
YieldReaction ConditionsOperation in experiment
95.8% With trifluoroacetic acid In dichloromethane at 0 - 10℃; The compound of formula II (65 g) was dissolved in 510 mL of methylene chloride and cooled to 0 to 10 ° C. 47 g of trifluoroacetic acid was slowly added dropwise to the system. The temperature was kept until the conversion of the raw material was completed. Sodium hydroxide solid , The system pH adjusted to 9 ~ 10, too Filtration, concentration and distillation gave 29.3 g of (R) -3-aminobutanol, yield 95.8percent
90% With hydrogenchloride In methanol; water at 25℃; for 6 h; Green chemistry Take 50g N-Boc-(R)-3-aminobutanol, dissolved in 350mL of concentrated hydrochloric acid / methanol system, the reaction for 6 hours at 25 °C, the GC detects completion of the reaction starting material, 54g of potassium carbonate was added, stirred for 1 hour, filtered The filtrate was concentrated and distilled under reduced pressure to give a product,m.p., 21 g, yield: 90percent, purity 99percent, ee.
0.5 g With hydrogenchloride In methanol at 25℃; To a solution of (R)-tert-butyl(4-hydroxybutan-2-yl) carbamate (1.3 g, 6.87 mmol) in methanol (30 mL) was added HC1 (30 mL, 4M in MeOH), stirred at 25°C overnight, concentrated to afford the title compound (0.5 g).
Reference: [1] Patent: CN106966912, 2017, A, . Location in patent: Paragraph 0025
[2] Patent: CN108424370, 2018, A, . Location in patent: Paragraph 0093; 0094
[3] Patent: WO2014/114249, 2014, A1, . Location in patent: Page/Page column 21
  • 4
  • [ 3775-73-3 ]
  • [ 61477-40-5 ]
YieldReaction ConditionsOperation in experiment
84.3% With sodium tetrahydroborate; trifluoroacetic acid In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice Under a nitrogen atmosphere, 120 g of sodium borohydride and 124 g of (R)-3-aminobutyric acid were placed in a reaction flask, 1.5 L of tetrahydrofuran was added, and the mixture was cooled with ice water. 506 g of trifluoroacetic acid was slowly added dropwise to the reaction flask, and the tail gas was absorbed by a sodium hydroxide solution. After the completion of the dropwise addition, the temperature was raised to 20 ° C until the starting material disappeared. The reaction was quenched by the addition of sodium hydroxide solution, and the layers were allowed to stand, and the organic phase was distilled to recover tetrahydrofuran. The aqueous phase was extracted with chloroform, and the combined extracts were dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product. Yield: 84.3percent, purity: 99.5percent, ee: 99.6percent.
54% With sodium tetrahydroborate; zinc(II) chloride In tetrahydrofuran at 20 - 60℃; for 3.5 h; Autoclave To a 50 L autoclave, 13 L of anhydrous tetrahydrofuran and 1067 g of anhydrous zinc chloride (with little exotherm) were added, Carefully add 590 grams of sodium borohydride (note the heat and gas). Stirred at room temperature for 30 minutes and then warmed to 50 to 60 ° C for 3 hours. After cooling to room temperature, 1280 g of a white solid obtained above was added in portions and the temperature was controlled at 10 to 40 ° C. After the addition was complete, the temperature was slowly raised to reflux for 24 hours. The system was turned into a gray suspension system, cooled to 10-15 ° C, and 640 ml of methanol and 200 g of 40percent aqueous sodium hydroxide solution were slowly added dropwise and the temperature was controlled at 10 to 40 ° C. After adding, stir at room temperature for 3 to 5 hours. Filtered, washed with THF and filtered to give a colorless liquid; Distillation distillation (10 to 65 ° C) Get a transparent viscous liquid R-3-aminobutanol 495 g, yield 54percent. Purity 99.2percent, 99.3percent.
Reference: [1] Patent: CN108689866, 2018, A, . Location in patent: Paragraph 0016-0020
[2] Patent: CN104370755, 2017, B, . Location in patent: Paragraph 0119; 0121
  • 5
  • [ 139243-54-2 ]
  • [ 61477-40-5 ]
YieldReaction ConditionsOperation in experiment
76%
Stage #1: With sodium hydrogencarbonate In water for 0.25 h; Cooling with ice
Stage #2: With potassium borohydride In methanol at 20℃; for 12 h;
Procedures and post-treatment in the same manner as in Example 11, by a 60g 3 (R) - amino butyric acid methyl ester hydrochloride, 42g 300mL methanol and potassium borohydride, a reduction reaction, to give 3 (R) - amino-1- (IV), colorless viscous liquid, 26.4 g, yield 76percent, ee value 99.4percent, content 99.2percent (GC method)
60 g of ethyl 3 (R) -aminobutyrate hydrochloride 63 mL of a 50percent aqueous solution of sodium hydrogencarbonate was carefully added with cooling with ice-water bath. After stirring for 15 minutes, the mixture was extracted three times with dichloromethane (100 mL x 3) , Dried over anhydrous sodium sulfate, filtered and concentrated to dryness (recovered methylene chloride can be applied in the same procedure as described in the next reaction). After adding 300 mL of ethanol to the residue,40 g of potassium borohydride was added in portions at room temperature with stirring, and the reaction was continued at room temperature with stirring,TLC follow the test, about 12 hours of complete reaction, vacuum distillation of ethanol recovery (the next batch reaction in this step the same procedure applied), to the residue by adding 200mL of water, stirring at room temperature with 2N hydrochloric acid carefully adjust PH value to 3- 4, washed three times with dichloromethane (100mL x 3), (combined washing liquid, by distillation of dichloromethane recovery, in the next batch of this step in the same application)The aqueous phase was then adjusted to pH 9 with 2N aqueous sodium carbonate solution, evaporated to dryness under reduced pressure,150 mL of absolute ethanol was added,After thorough stirring, filtration,And then washed with 50mL absolute ethanol filter cake,The organic phases were combined,The ethanol was recovered by distillation at atmospheric pressure (the ethanol fraction was recovered by combining the pre-distillate from the vacuum distillation product,In the next batch of reaction to the same procedure used in this step),Then vacuum distillation,The 59-60 ° C / 10 mm Hg fraction was collected,To give 3 (R) -amino-1-butanol (IV),Colorless viscous liquid, 24.5 g, yield 77percent, ee value 99.2percent, content 99.1percent (GC method)
Reference: [1] Patent: CN105001098, 2016, B, . Location in patent: Paragraph 0091; 0092; 0093; 0094
  • 6
  • [ 899806-42-9 ]
  • [ 61477-40-5 ]
Reference: [1] Patent: WO2006/76595, 2006, A1, . Location in patent: Page/Page column 169-170
  • 7
  • [ 6078-06-4 ]
  • [ 61477-40-5 ]
YieldReaction ConditionsOperation in experiment
> 99 % ee With hydrogen In tetrahydrofuran at 80℃; for 14 h; Example 9Hydrogenation of Methyl (R)-3-aminobutanoate A ruthenium complex 1 (0.333 mmol) was charged into a 100-mL autoclave equipped with a stirrer, and air inside the autoclave was replaced with nitrogen. Tetrahydrofuran (40 mL) and methyl (R)-3-aminobutanoate (100 mmol, 99percent ee or more) were charged thereinto. Then, the mixture was subjected to hydrogenation at a hydrogen pressure of 3.5 MPa to 5 MPa at 80° C. for 14 hours. The reaction liquid was concentrated, and the obtained residue was distilled. Thus, (R)-3-aminobutanol (7.39 g; boiling point of 84 to 86° C./14 Torr) was obtained. The obtained alcohol had an optical purity of 99percent ee or more.
Reference: [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 1, p. 92 - 96
[2] Patent: US2010/63294, 2010, A1, . Location in patent: Page/Page column 13-14
  • 8
  • [ 590-90-9 ]
  • [ 61477-40-5 ]
YieldReaction ConditionsOperation in experiment
0.45 g With SEC-BUTYLAMINE; magnesium chloride In aq. phosphate buffer; dimethyl sulfoxide at 15℃; for 24 h; Enzymatic reaction A mixture of 0.9 gm enzyme ECS-ATA-134 and 7.5 ml PLP solution was added to asol uti on of phosphate buffer (15 ml, of example 2), secondary butyl amine (20 ml) andmagnesium chloride (5 ml) followed Li addition of a substrate solution (0.6 gm 4-Hydroxy butanone in S ml Dimethyl sulfoxide). The reaction mixture was stirred at 1Sfor 24 hours. The reaction mixture was extracted with ethyl acetate and the solvent wasremav’ed by distillation to obtain (R)-3-aminobutan-1 -ol. Y ield: 0.45 gm, 100percent R-isomer.
Reference: [1] Patent: WO2018/20380, 2018, A1, . Location in patent: Page/Page column 6
  • 9
  • [ 120686-16-0 ]
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Reference: [1] Patent: US2003/73723, 2003, A1,
  • 10
  • [ 60920-20-9 ]
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Reference: [1] The Journal of organic chemistry, 1977, vol. 42, # 9, p. 1650 - 1652
  • 11
  • [ 245728-81-8 ]
  • [ 61477-40-5 ]
Reference: [1] Tetrahedron Asymmetry, 1999, vol. 10, # 11, p. 2213 - 2224
  • 12
  • [ 866395-51-9 ]
  • [ 87-41-2 ]
  • [ 61477-40-5 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 38, p. 9031 - 9041
  • 13
  • [ 116173-78-5 ]
  • [ 61477-40-5 ]
Reference: [1] Tetrahedron Letters, 1988, vol. 29, # 2, p. 231 - 234
  • 14
  • [ 5303-65-1 ]
  • [ 61477-39-2 ]
  • [ 61477-40-5 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 20, p. 2895 - 2898
  • 15
  • [ 24424-99-5 ]
  • [ 61477-40-5 ]
  • [ 167216-17-3 ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine In dichloromethane at 20 - 24℃; for 4 h; Example 36
Preparation of (R)-tert-butyl(4-hydroxybutan-2-yl)carbamate (C56)
Triethylamine (2.35 mL, 16.8 mmol) and di-tert-butyl dicarbonate (2.50 g, 12.3 mmol) were added to a solution of (R)-3-aminobutan-1-ol (1.00 g, 11.2 mmol) in dichloromethane (10 mL).
The reaction mixture was stirred for 4 hours at room temperature.
The reaction mixture was concentrated, the residue poured into ice water, and then extracted with ethyl acetate.
The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated.
Purification by flash column chromatography using 20percent ethyl acetate/petroleum ether as eluent provided the title compound as a white solid (1.7 g, 80percent): 1H NMR (400 MHz, DMSO-d6) δ 6.62 (d, J=8.4 Hz, 1H), 4.43-4.31 (m, 1H), 3.55-3.52 (m, 1H), 3.40-3.38 (m, 2H), 1.55-1.48 (m, 2H), 1.43 (s, 9H), 1.01 (d, J=6.8 Hz, 3H).
Reference: [1] Patent: US2017/210723, 2017, A1, . Location in patent: Paragraph 0537-0538
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