[ CAS No. 30414-53-0 ]

Name: 30414-53-0|Methyl 3-oxovalerate|98%
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Quality Control of [ 30414-53-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 30414-53-0 ]

CAS No. :	30414-53-0	MDL No. :	MFCD00011705
Formula :	C₆H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XJMIXEAZMCTAGH-UHFFFAOYSA-N
M.W :	130.14	Pubchem ID :	121699
Synonyms :

Calculated chemistry of [ 30414-53-0 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	32.44
TPSA :	43.37 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.55
Log Po/w (XLOGP3) :	0.44
Log Po/w (WLOGP) :	0.53
Log Po/w (MLOGP) :	0.28
Log Po/w (SILICOS-IT) :	0.73
Consensus Log Po/w :	0.71

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.66
Solubility :	28.5 mg/ml ; 0.219 mol/l
Class :	Very soluble
Log S (Ali) :	-0.92
Solubility :	15.7 mg/ml ; 0.121 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.06
Solubility :	11.2 mg/ml ; 0.0861 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.36

Safety of [ 30414-53-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H227-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 30414-53-0 ]

* 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 [ 30414-53-0 ]
Downstream synthetic route of [ 30414-53-0 ]

[ 30414-53-0 ] Synthesis Path-Upstream 1~32

1
[ 30414-53-0 ]
[ 3473-63-0 ]
[ 124703-78-2 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 5, p. 1369 - 1370
[2] Patent: US5278175, 1994, A,

2
[ 30414-53-0 ]
[ 5734-67-8 ]

Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2429 - 2439

3
[ 30414-53-0 ]
[ 95-54-5 ]
[ 52099-72-6 ]

Reference： [1] Patent: US5652246, 1997, A,

4
[ 30414-53-0 ]
[ 50405-45-3 ]

Reference： [1] Heterocycles, 2000, vol. 53, # 3, p. 549 - 552

5
[ 41340-36-7 ]
[ 30414-53-0 ]
[ 41340-25-4 ]

Reference： [1] Croatica Chemica Acta, 2016, vol. 89, # 4,

6
[ 79-03-8 ]
[ 30414-53-0 ]

Yield	Reaction Conditions	Operation in experiment
71%	With calcium hydroxide In dichloromethane; ammonia; butanone	EXAMPLE 3 Under the same conditions as in Example 1, 116 g (1.0 mol) of methyl acetoacetate in a mixture of 520 ml of methylene chloride and 30 ml of methyl ethyl ketone were reacted with 77.8 g (1.05 mol) of calcium hydroxide and 106.5 g (1.15 mol) of propionyl chloride. The pH in the subsequent reaction with ammonia was adjusted to 9.1. This gave 117 g (GC purity 79.0percent) of methyl propionylacetate (yield 71.0percent).

Reference： [1] Patent: US5194671, 1993, A,

7
[ 105-45-3 ]
[ 74-88-4 ]
[ 30414-53-0 ]

Reference： [1] Tetrahedron, 2015, vol. 71, # 39, p. 7459 - 7469
[2] Journal of the American Chemical Society, 1974, vol. 96, p. 1082 - 1087
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 10, p. 1237 - 1244

8
[ 10191-25-0 ]
[ 30414-53-0 ]

Reference： [1] Patent: US4761420, 1988, A,
[2] Patent: US4761420, 1988, A,
[3] Patent: US4761420, 1988, A,

9
[ 24342-04-9 ]
[ 30414-53-0 ]

Reference： [1] Tetrahedron Letters, 2010, vol. 51, # 32, p. 4281 - 4283

10
[ 79-03-8 ]
[ 30414-53-0 ]

Reference： [1] Patent: US5144057, 1992, A,

11
[ 37517-81-0 ]
[ 925-90-6 ]
[ 30414-53-0 ]

Reference： [1] Organic Letters, 2008, vol. 10, # 22, p. 5269 - 5271

12
[ 616-38-6 ]
[ 78-93-3 ]
[ 30414-53-0 ]

Reference： [1] Chemical Communications, 2011, vol. 47, # 39, p. 11143 - 11145
[2] Organic and Biomolecular Chemistry, 2011, vol. 9, # 3, p. 739 - 743
[3] Journal of Organic Chemistry, 2017, vol. 82, # 20, p. 10883 - 10897

13
[ 67-56-1 ]
[ 64074-05-1 ]
[ 30414-53-0 ]

Reference： [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 3, p. 823 - 825
[2] Patent: WO2010/120854, 2010, A1, . Location in patent: Page/Page column 121

14
[ 883528-73-2 ]
[ 30414-53-0 ]

Reference： [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2229,2233

15
[ 186581-53-3 ]
[ 10191-25-0 ]
[ 30414-53-0 ]

Reference： [1] Journal of the American Chemical Society, 1944, vol. 66, p. 864

16
[ 38330-80-2 ]
[ 802294-64-0 ]
[ 30414-53-0 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 2, p. 171 - 176

17
[ 20577-62-2 ]
[ 30414-53-0 ]

Reference： [1] Journal of the American Chemical Society, 1948, vol. 70, p. 2595
[2] Journal of the American Chemical Society, 1948, vol. 70, p. 2595

18
[ 10467-10-4 ]
[ 105-34-0 ]
[ 30414-53-0 ]

Reference： [1] Chemische Berichte, 1985, vol. 118, # 9, p. 4073 - 4085

19
[ 67-56-1 ]
[ 66696-76-2 ]
[ 30414-53-0 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986, p. 2137 - 2142

20
[ 17448-81-6 ]
[ 124-41-4 ]
[ 30414-53-0 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1963, vol. 21, p. 186 - 197
[2] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1964, p. 145 - 146[3] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1964, p. 164 - 166

21
[ 56009-31-5 ]
[ 30414-53-0 ]

Reference： [1] Chemistry - A European Journal, 2017, vol. 23, # 51, p. 12636 - 12645

22
[ 186581-53-3 ]
[ 78-93-3 ]
[ 17094-21-2 ]
[ 30414-53-0 ]

Reference： [1] Tetrahedron Letters, 1980, vol. 21, # 20, p. 1967 - 1970

23
[ 7647-01-0 ]
[ 883528-73-2 ]
[ 30414-53-0 ]

Reference： [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2229,2233

24
[ 30414-53-0 ]
[ 106-96-7 ]
[ 100330-50-5 ]

Reference： [1] Chemical Communications, 2017, vol. 53, # 24, p. 3481 - 3484

25
[ 30414-53-0 ]
[ 180287-02-9 ]

Reference： [1] Patent: EP1174415, 2002, A1, . Location in patent: Page 4, 5
[2] Patent: EP1174415, 2002, A1, . Location in patent: Page 7
[3] Patent: EP1174415, 2002, A1, . Location in patent: Page 6
[4] Patent: EP1174415, 2002, A1, . Location in patent: Page 6
[5] Patent: EP1431269, 2004, A1, . Location in patent: Page column 5
[6] Organic Letters, 2015, vol. 17, # 5, p. 1090 - 1093
[7] Patent: TW2016/2115, 2016, A, . Location in patent: Paragraph 5047 - 5049

26
[ 30414-53-0 ]
[ 227183-98-4 ]
[ 180287-02-9 ]

Reference： [1] Patent: EP1174415, 2002, A1, . Location in patent: Page 5
[2] Patent: EP1174415, 2002, A1, . Location in patent: Page 6

27
[ 30414-53-0 ]
[ 180287-02-9 ]

Reference： [1] Patent: EP1174415, 2002, A1, . Location in patent: Page 4 - 5

28
[ 30414-53-0 ]
[ 439809-77-5 ]
[ 439809-76-4 ]
[ 196202-01-4 ]
[ 196202-02-5 ]
[ 180287-02-9 ]

Reference： [1] Patent: EP1362842, 2003, A1, . Location in patent: Page/Page column 6-8

29
[ 30414-53-0 ]
[ 196202-01-4 ]
[ 196202-02-5 ]
[ 180287-02-9 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 2002, vol. 67, # 10, p. 1416 - 1420

30
[ 30414-53-0 ]
[ 196202-01-4 ]
[ 196202-02-5 ]
[ 180287-02-9 ]

Reference： [1] Journal of Fluorine Chemistry, 2003, vol. 120, # 2, p. 173 - 183

31
[ 30414-53-0 ]
[ 496062-16-9 ]

Reference： [1] Patent: US2018/153859, 2018, A1,
[2] Patent: US2018/153860, 2018, A1,

32
[ 30414-53-0 ]
[ 259654-73-4 ]

Reference： [1] Patent: US2018/153860, 2018, A1,
[2] Patent: US2018/153859, 2018, A1,

[ 30414-53-0 ] Synthesis Path-Downstream 1~48

1
[ 455-14-1 ]
[ 30414-53-0 ]
[ 749921-32-2 ]

Yield	Reaction Conditions	Operation in experiment
77.1%	With boron trifluoride diethyl etherate In toluene for 5h; Heating / reflux;	1 Example 1; Preparation of methyl 3- (4-trifluoromethylphenylamino)-2- pentenoate In a 500-ml flask, 4-trifluoromethylaniline (80.6g, 0. 5mol), methyl 3-oxopentanoate (65. 1g, 0. 5mol) and toluene 400ML were placed. To this solution was added boron trifluoride etherate (1.42g, 10MMOL), and the resulting mixture was heated under a reduced pressure of 8kPa. The reaction mixture was heated for 5 hours under reflux, while water produced was removed out of the reaction system by using a Dean-Stark trap. Then, the heating was discontinued and nitrogen was leaked. After cooling, the solvent was removed by distillation by using a rotary evaporator. The residue was then distilled under reduced pressure to give 105.3g of the title compound. The yield was 77. 1%. 1H-NMR (CDC13, 8PPM) : 10.52 (bs, 1H), 7.57 (d, J=8.5Hz, 2H), 7.16 (d, J=8.5Hz, 2H), 4.85 (s, 1H), 3.70 (s, 3H), 2.42 (d, J=7. 4Hz, 2H), 1.08 (t, J=7.4Hz, 3H).
77.8%	With Amberlyst No_. 31 WET type In toluene at 100℃; for 11h; Heating / reflux;	13 Example 13; Preparation of methyl 3- (4-trifluoromethylphenylamino)-2- pentenoate In a 500ML-FLASK were placed 4-trifluoromethylanline (48.3g, 0. 30mol), methyl 3-oxopentanoate (43. 0G, 0. 33mol) and toluene (192ml). To this solution was added 4.8g of solid acid catalyst (AMBERLYST No. 31 WET type, product of Rohm and Haas Co. ), and the resulting mixture was heated in a bath kept at 100 C under a reduced pressure of 25kPa for 11 hours, while removing the water formed under reflux by using a Dean-Stark trap. The heating was then discontinued, nitrogen leaked in, and the reaction mixture cooled. The catalyst was filtered off and the solvent evaporated off by using a rotary evaporator, and the residue was distilled under reduced pressure to give 213g of the title compound. The yield was 77.8%. THE 1H-NMR spectrum was identical to that of Example 1.
77.6%	With tri-(tert-butyl)borate In toluene at 100℃; for 6h; Heating / reflux;	14 Example 14; Preparation of methyl 3- (4-trifluoromethylphenylamino)-2- pentenoate 4-Trifluoromethylanline (161g, 1. 00MOL), methyl 3- oxopentanoate (143g, 1. 10mol) and toluene (640ml) were placed in a 2L-flask. To this solution was added tri (tert- butyl) borate (22.7g, 0. 10MOL), and the resulting mixture was heated in a bath kept at 100 C under a reduced pressure of 27kPa for 6 hours, while removing the water formed by refluxing by using a Dean-Stark trap. The heating was then discontinued, nitrogen leaked in, and the reaction mixture cooled. The solvent was evaporated off by using a rotary- evaporator, and the residue was distilled under reduced pressure to give 212g of the title compound. The yield was 77. 6%. THE 1H-NMR spectrum was identical to that of Example 1.

75.8%	With toluene-4-sulfonic acid In toluene at 100℃; for 15h; Heating / reflux;	12 Example 12; Preparation of methyl 3- (4-trifluoromethylphenylamino)-2- pentenoate In a 2L-flask were placed 4-trifluoromethylaniline (161g, 1. 00MOL), methyl 3-oxopentanoate (143g, 1. 10mol) and toluene (640 ml). To this solution was added p- toluenesulfonic acid monohydrate (3.2g, 0. 017MOL), and the resulting mixture was heated in a bath kept at 100 C under a reduced pressure of 27kPa, while the water generated was taken out of the reaction system by using a Dean-Stark trap under reflux. After 15 hours, the heating was discontinued, nitrogen leaked in, and the reaction mixture cooled. The solvent was evaporated by means of a rotary- evaporator, and the residue was distilled under reduced pressure to give 207g of the title compound. The yield was 75.8%. THE 1H-NMR spectrum was identical to that of Example 1.
72.8%	With acetic acid In toluene at 100℃; for 10.5h; Heating / reflux;	11 Example 11; Preparation of methyl 3- (4-trifluoromethylphenylamino)-2- pentenoate In a IL-flask were placed 4-trifluoromethylaniline (161g, 1. 00MOL), methyl 3-oxopentanoate (130g, 1. 00MOL) and toluene (160ML). To this solution was added acetic acid (16g, 0. 27mol), and the resulting mixture was heated in a bath kept at 100 C under a reduced pressure of 19kPa for 3.5 hours, while the water generated was taken out of the reaction system by using a Dean-Stark trap under reflux. Acetic acid (16g, 0. 27MOL) was then added, and reflux was continued for 4.5 hours. Acetic acid (8g, 0. 13mol) was then added again, and reflux was continued for another 2.5 hours. The heating was then discontinued, nitrogen leaked in, and the reaction mixture cooled. After distillation of the solvent and acetic acid under reduced pressure, the residue was distilled under reduced pressure to give 199G of the title compound. The yield was 72.8%. THE 1H-NMR spectrum was identical to that of Example 1.
	With toluene-4-sulfonic acid In cyclohexane for 7h; Heating;

Reference： [1]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - WO2004/74255, 2004, A2 Location in patent: Page 74-75
[2]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - WO2004/74255, 2004, A2 Location in patent: Page 82-83
[3]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - WO2004/74255, 2004, A2 Location in patent: Page 83
[4]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - WO2004/74255, 2004, A2 Location in patent: Page 82
[5]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - WO2004/74255, 2004, A2 Location in patent: Page 81-82
[6]Bradbury; Allott; Dennis; Fisher; Major; Masek; Oldham; Pearce; Rankine; Revill; Roberts; Russell [Journal of Medicinal Chemistry, 1992, vol. 35, # 22, p. 4027 - 4038]

2
[ 30414-53-0 ]
[ 60789-54-0 ]
[ 129512-09-0 ]

Reference： [1]Synthesis,1990,p. 382 - 386

3
[ 30414-53-0 ]
[ 3473-63-0 ]
[ 124703-78-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium methylate; In methanol;	(i) 6-Ethylpyrimidin-4(3H)-one To a solution of sodium methoxide (4.19 kg, 77.6 mol) and formamidine acetate (3.0 kg, 28.8 mol) in methanol (45 L) at 5-10 C. was added slowly a solution of methyl propionylacetate (2.5 kg, 19.2 mol) in methanol (10 L) maintaining the temperature below 20 C. throughout the addition. The resulting mixture was stirred at room temperature overnight after which time the pH was adjusted to 7 by the addition of concentrated hydrochloric acid. The reaction mixture was concentrated under reduced pressure to ca.10 L in volume, diluted with water (10 L) and was extracted with 2-butanone (2*30 L). The combined organic extracts were concentrated under reduced pressure to ca. 2 L in volume and diluted with ethyl acetate (4 L). The desired product crystallized from the solution (2.4 kg, 70%) and was recrystallized from isopropanol to yield a product of m.p. 132-134 C. Found: C,58.45; H,6.37; N,22.41; C6 H8 N2 O requires: C,58.05; H,6.50; N,22.57%.

Reference： [1]Journal of Heterocyclic Chemistry,1992,vol. 29,p. 1369 - 1370
[2]Patent: US5278175,1994,A

4
[ 30414-53-0 ]
methyl (3R)-3-hydroxypentanoate [ No CAS ]
[ 42558-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;dichloro[(R)-N-bis(3,5-dimethylphenyl)phosphino-N-methyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine](triphenylphosphine)ruthenium; In methanol; at 20℃; under 16274.9 Torr; for 6h;Conversion of starting material;	Complex 5A-g from Example 9 (2.8 mg; 0.0025 mmol; 0.005 equiv) was placed in a reaction vessel, which was pressurized with argon and vented five times. Argon-degassed methanol (2 mL) was added and the mixture was stirred for 15 minutes. Methyl propionylacetate (63 μL; 0.5 mmol) dissolved in 2 mL of argon-degassed methanol was added and was washed in with 1.0 mL of argon-degassed methanol. The reaction mixture was pressurized with argon and vented five times and then pressurized to 20.7 barg (300 psig) with hydrogen and stirred at ambient temperature for 6 hours. The vessel was vented, then pressurized with argon and vented five times, and the solution was assayed by chiral GC to indicate 100% conversion to methyl (R)-3-hydroxypentanoate with 79.3% ee.

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 2657 - 2660
[2]Tetrahedron Letters,1989,vol. 30,p. 2245 - 2246
[3]Chemistry Letters,1987,p. 679 - 682
[4]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 875 - 879
[5]Chemistry Letters,1987,p. 1267 - 1270
[6]Chemistry Letters,1987,p. 679 - 682
[7]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 2473 - 2477
[8]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 1414 - 1419
[9]Tetrahedron Letters,1997,vol. 38,p. 6603 - 6606
[10]Tetrahedron Letters,1990,vol. 31,p. 267 - 270
[11]Tetrahedron Letters,1989,vol. 30,p. 2245 - 2246
[12]Chemistry Letters,1987,p. 1267 - 1270
[13]Tetrahedron Letters,1997,vol. 38,p. 6603 - 6606
[14]Chemistry Letters,1998,p. 1257 - 1258
[15]Journal of Organic Chemistry,2000,vol. 65,p. 2586 - 2587
[16]Journal of the American Chemical Society,2001,vol. 123,p. 1547 - 1555
[17]Bulletin of the Chemical Society of Japan,2002,vol. 75,p. 355 - 363
[18]Bulletin of the Chemical Society of Japan,2002,vol. 75,p. 355 - 363
[19]Angewandte Chemie - International Edition,2004,vol. 43,p. 5066 - 5069
[20]Advanced Synthesis and Catalysis,2005,vol. 347,p. 1978 - 1986
[21]Advanced Synthesis and Catalysis,2006,vol. 348,p. 1157 - 1160
[22]Tetrahedron Letters,2006,vol. 47,p. 4033 - 4035
[23]Tetrahedron Letters,1985,vol. 26,p. 4213 - 4216
[24]Advanced Synthesis and Catalysis,2003,vol. 345,p. 160 - 164
[25]Patent: US6939981,2005,B1 .Location in patent: Page/Page column 16-17
[26]Advanced Synthesis and Catalysis,2009,vol. 351,p. 725 - 732
[27]Advanced Synthesis and Catalysis,2013,vol. 355,p. 209 - 219
[28]Advanced Synthesis and Catalysis,2013,vol. 355,p. 209 - 219
[29]European Journal of Inorganic Chemistry,2017,vol. 2017,p. 2762 - 2773

5
[ 30414-53-0 ]
[ 42558-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;dichloro[(S)-N-diphenylphosphino-N-methyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine](triphenylphosphine)ruthenium; In methanol; at 20℃; under 16274.9 Torr; for 6h;Conversion of starting material;	Complex 5B-a from Example 1 (2.6 mg; 0.0025 mmol; 0.005 equiv) was placed in a reaction vessel, which was pressurized with argon and vented five times. Argon-degassed methanol (2 mL) was added and the mixture was stirred for 15 minutes. Methyl propionylacetate (63 μL; 0.5 mmol) dissolved in 2 mL of argon-degassed methanol was added and was washed in with 1.0 mL of argon-degassed methanol. The reaction mixture was pressurized with argon and vented five times and then pressurized to 20.7 barg (300 psig) with hydrogen and stirred at ambient temperature for 6 hours. The vessel was vented, then pressurized with argon and vented five times, and the solution was assayed by chiral GC to indicate 100% conversion to methyl (S)-3-hydroxypentanoate with 86.2% ee. Chiral GC [30 m×0.25 mm Cyclosil-B (J&W Scientific), 0.25 μm film thickness, 70 C. isothermal]: tR=9.72 min (methyl propionylacetate), tR=10.34 min [methyl (S)-3-hydroxypentanoate], tR=10.80 min [methyl (R)-3-hydroxypentanoate].
	With hydrogen;dichloro(benzene)ruthenium(II) dimer; (11bS,11'bS)-4,4'-(9,9-dimethyl-9H-xanthene-4,5-diyl)-bis-dinaphtha[2,1-d:1',2'-f][1,3,2]dioxaphosphepin; In ethanol; dichloromethane; at 60℃; under 45004.5 Torr; for 20h;Product distribution / selectivity;	[Ru(benzene)Cl2]2 (N) (16 mg, 0.032 mmol) and a diphosphonite (0.067 mmol) were introduced into a 25 ml Schlenk tube. The tube was purged three times with argon before dry dimethylformamide (DMF) (3 ml) was added. The resulting mixture was heated to 100 C. for 30 minutes and then cooled to 60 C. The solvent was removed under reduced pressure, and the catalyst was obtained as a pale green-yellow solid. This catalyst was dissolved in dry dichloromethane (8 ml) and distributed uniformly between 8 vials (in each case 1 ml), which had already been purged three times with argon. A ketone, such as a β-keto ester (III) (0.8 mmol), was introduced into each vessel, then in each case 3 ml of ethanol were added. These were then transferred to a high-pressure autoclave. Once it had been purged three times with H2, the autoclave was adjusted to a pressure 60 bar with H2, and the reactions were stirred magnetically at 60 C. over 20 h. The autoclave was subsequently cooled to room temperature and H2 was cautiously discharged. Samples were taken from each reaction solution and put through a small amount of silica gel before the GC analysis in order to determine the conversions and ee values. The absolute configuration was determined in comparison to known compounds described in the literature.
	With methanesulfonic acid; hydrogen;[RuCl(p-cymene)(VIIa)]Cl; In methanol; at 100℃; under 7500.75 Torr; for 24.3333h;Ultrasonic treatment;Product distribution / selectivity;	A solution of 3.8 ml of methanol and 3 g (23 mmol) of methyl 3-oxopentanoate was treated with [RuCl(p-cymene)(VIIa)]Cl in the manner described in Example 8. This gave 3.03 g of methyl (S)-3-hydroxypentanoate. 99.9% ee (GC); >99% chemical purity.

	With methanesulfonic acid; hydrogen;RuBr2(VIIa); In methanol; at 100℃; under 7500.75 Torr; for 24.3333h;Ultrasonic treatment;Product distribution / selectivity;	A solution of 3.8 ml of methanol and 3 g (23 mmol) of methyl 3-oxopentanoate was treated with 0.0115 mmol of [RuBr2(VIIa)] in the manner described in Example 8. This gave 2.88 g of methyl (S)-3-hydroxypentanoate. 99.5% ee (GC); 95% chemical purity.
	With methanesulfonic acid; hydrogen;[RuCl(benzene)(VIIa)]Cl; In methanol; at 100℃; under 7500.75 Torr; for 24.3333h;Ultrasonic treatment;Product distribution / selectivity;	A solution of 3.8 ml of methanol and 3 g (23 mmol) of methyl 3-oxopentanoate was treated with 0.0115 mmol of [RuCl(benzene)(VIIa)]Cl in the manner described in Example 8. This gave 3.03 g of methyl (S)-3-hydroxy-pentanoate. 99.6 % ee (GC); >99 % chemical purity.
	With dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II); hydrogen; In methanol; at 100℃; under 3800.26 Torr; for 48h;	Synthesis of 1-Azido-3-Pentanol (31) (Scheme 14) A solution of methyl-3-oxo-pentanoate (31) (20 g) noyori hydrogenation with RuCl2 [(S)-BINAP] (60 mg), in methanol was added. The flask was charged with hydrogen gas (5 atm) at 100 C. The resulting suspension was vigorously stirred for 48 hours. The reaction mixture was diluted with methanol and the combined organic layers were filtered through a Celite pad. The combined organic phases were evaporated in a rotary evaporator to yield the product (S) isomer of methyl-3-hydroxy-pentanoate (32). The methyl-3-hydroxy-pentanoate (secondary alcohol-32) was protected with TBDMSCl in the presence of imidazole in dichloro methane. The reaction mixture was stirred for 24 hours at room temperature. This reaction was quenched with aqueous saturated sodium bicarbonate and extracted with dichloro methane. The combined organic phases were dried over Na2SO4 and the combined organic phases were evaporated in a rotary evaporator to yield the TBS protected product (33). A stirred solution of ester was reduced with di-isobutyl aluminum hydride in dichloro methane at -78 C. for 5 hours. This reaction mixture was quenched with saturated aqueous sodium potassium tartarate. The combined organic and aqueous layers were filtered and organic layer was separated by separating funnel. The aqueous layer was extracted with dichloro methane. The combined organic phases were dried over Na2SO4 and the combined organic phases were evaporated in a rotary evaporator to yield the product primary alcohol (34) as a pale yellow liquid. The primary alcohol was protected with methane sulfonyl chloride in the presence of TEA in dichloromethane. The reaction mixture was stirred for 4 hours at 0 C. This reaction was quenched with aqueous saturated sodium bicarbonate and extracted with dichloro methane. The combined organic phases were dried over Na2SO4 and the combined organic phases were evaporated in a rotary evaporator to yield the methane sulfonyl protected product (35). The methane sulfonyl protected primary alcohol was stirred at 70 C. with NaN3 in DMF for 16 hours. A stirred solution of TBS protected secondary alcohol. This reaction was quenched with pre cooled ice water and extracted with diethyl ether. The combined organic phases were dried over Na2SO4. The combined organic phases were evaporated in a rotary evaporator to yield the azido product as a colorless liquid (36). This was deprotected with TBAF in tetrahydrofuran at room temperature. This reaction was quenched with saturated ammonium chloride solution and extracted with diethyl ether; the combined organic phases were dried over Na2SO4 and evaporated on rotary evaporator to yield the product 1-azido-3-pentanol (36A) as a colorless liquid.
> 99.5%Chromat.	With hydrogen; In isopropyl alcohol; at 50℃; under 30003 Torr; for 10h;Autoclave; Glovebox;	General procedure: As a typical run for asymmetric hydrogenation of β-keto esters, 0.026 g Ru/5-BINAPPOPs-1 catalyst, 0.20 g methyl acetoacetate, and 2 mL of isopropanol (ipro) were added to a 30-mL autoclave in a glove box. After the reactor was purged with H2 four times, its pressure was finally adjusted to the desired value, heated from room temperature to the reaction temperature of 50 C, and stirred for 10 h. The catalyst was separated by centrifugation, and the product was analysed using gas chromatography (GC; Agilent 7890B gas chromatograph equipped with a flame ionization detector and a Cyclosil-B capillary column).

Reference： [1]Tetrahedron Asymmetry,1991,vol. 2,p. 569 - 592
[2]Tetrahedron Asymmetry,1994,vol. 5,p. 675 - 690
[3]Journal of Organic Chemistry,2004,vol. 69,p. 7577 - 7581
[4]Chemical Communications,2019,vol. 56,p. 157 - 160
[5]European Journal of Organic Chemistry,2014,vol. 2014,p. 323 - 330
[6]European Journal of Organic Chemistry,2014,vol. 2014,p. 323 - 330
[7]Synlett,2011,p. 191 - 194
[8]Journal of the American Chemical Society,1987,vol. 109,p. 5856 - 5858
[9]Tetrahedron Letters,1995,vol. 36,p. 4801 - 4804
[10]Journal of the American Chemical Society,1995,vol. 117,p. 4423 - 4424
[11]Tetrahedron,2001,vol. 57,p. 2563 - 2568
[12]Journal of the American Chemical Society,2001,vol. 123,p. 1547 - 1555
[13]Patent: US6359165,2002,B1 .Location in patent: Page column 13
[14]Patent: US6939981,2005,B1 .Location in patent: Page/Page column 14
[15]Patent: US2008/255355,2008,A1 .Location in patent: Page/Page column 8-9
[16]Patent: US2005/250951,2005,A1 .Location in patent: Page/Page column 12
[17]Patent: US2005/250951,2005,A1 .Location in patent: Page/Page column 13
[18]Patent: US2005/250951,2005,A1 .Location in patent: Page/Page column 12
[19]Advanced Synthesis and Catalysis,2013,vol. 355,p. 209 - 219
[20]Patent: US9250238,2016,B2 .Location in patent: Page/Page column 106; 107; 108
[21]Cuihua Xuebao/Chinese Journal of Catalysis,2017,vol. 38,p. 890 - 897

6
[ 30414-53-0 ]
[ 60789-54-0 ]
[ 814-49-3 ]
[ 129512-07-8 ]

Reference： [1]Synthesis,1990,p. 382 - 386

7
[ 30414-53-0 ]
[ 106675-70-1 ]
(4-hydroxy-3-methyl-5-oxo-5<i>H</i>-furan-2-ylidene)-acetic acid methyl ester [ No CAS ]
[ 236389-55-2 ]

Reference： [1]Angewandte Chemie - International Edition,1999,vol. 38,p. 1803 - 1805

8
[ 30414-53-0 ]
[ 106675-70-1 ]
[ 236389-55-2 ]

Reference： [1]Synlett,2000,p. 844 - 846
[2]Chemistry - A European Journal,2000,vol. 6,p. 3204 - 3214

9
[ 30414-53-0 ]
[ 74-88-4 ]
[ 524735-91-9 ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium methylate In methanol at 20℃; for 48h;

Reference： [1]Jabin, Ivan; Monnier-Benoit, Nicolas; Le Gac, Stéphane; Netchitaïlo, Pierre [Tetrahedron Letters, 2003, vol. 44, # 3, p. 611 - 614]

10
[ 30414-53-0 ]
[ 50405-45-3 ]

Reference： [1]Heterocycles,2000,vol. 53,p. 549 - 552

11
[ 30414-53-0 ]
[ 129705-30-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 100 percent / H₂, <Ru((S)-(-)-BINAP> cat. / methanol; CH₂Cl₂ / 48 h / 25 °C / 77572.2 Torr 2: aq. KOH / ethanol / 48 h / 25 °C 3: 50 percent / NaOMe / methanol / 0 °C / electrochemical coupling, pH 5.38

Reference： [1]Burk; Feaster; Harlow [Tetrahedron Asymmetry, 1991, vol. 2, # 7, p. 569 - 592]

12
[ 30414-53-0 ]
[ 129619-37-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 100 percent / H₂, <Ru((R)-(+)-BINAP> cat. / methanol; CH₂Cl₂ / 48 h / 25 °C / 77572.2 Torr 2: 97 percent / aq. KOH / ethanol / 48 h / 25 °C 3: 36 percent / NaOMe / methanol / 0 °C / electrochemical coupling, pH 5.38

Reference： [1]Burk; Feaster; Harlow [Tetrahedron Asymmetry, 1991, vol. 2, # 7, p. 569 - 592]

13
[ 30414-53-0 ]
[ 136705-66-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 100 percent / H₂, <Ru((S)-(-)-BINAP> cat. / methanol; CH₂Cl₂ / 48 h / 25 °C / 77572.2 Torr 2: aq. KOH / ethanol / 48 h / 25 °C 3: NaOMe / methanol / 0 °C / electrochemical coupling, pH 5.38

Reference： [1]Burk; Feaster; Harlow [Tetrahedron Asymmetry, 1991, vol. 2, # 7, p. 569 - 592]

14
[ 30414-53-0 ]
[ 626-43-7 ]
methyl 3-(3,5-dichlorophenylamino)-2-pentenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.8%	With toluene-4-sulfonic acid; In toluene; at 100℃; under 157.516 Torr; for 3h;Heating / reflux;	In a 300mL-flask were placed 3,5-dichloroaniline (25. 0G, 154MMOL), methyl 3-oxopentanoate (22. 1g, 170MMOL) and toluene (160ML). To this solution was added p- toluenesulphonic acid monohydrate (0.59g, 3. 1MMOL), and the resulting mixture was heated in a bath kept at 100 C under a reduced pressure of 21KPA for 3 hours, while the water generated was taken out of the reaction system by using a Dean-Stark trap under reflux. p-Toluenesulphonic acid monohydrate (0.59g, 3. 1MMOL) was then added, and reflux was continued for 1 hour. The heating was then discontinued, nitrogen leaked in, and the reaction mixture cooled. After distillation of the solvent under reduced pressure, the residue was distilled under reduced pressure to give 27.4g of the title compound. The yield was 64. 8%. 1H-NMR (500MHZ, CDC13, 8PPM) : 10. 35 (bs, 1H), 7.13 (t, J=1. 8HZ, 1H), 6.98 (d, J=1. 8HZ, 2H), 4.83 (s, 1H), 3.69 (s, 3H), 2.37 (q, J=7. 4HZ, 2H), 1.08 (t, J=7.4Hz, 3H).

Reference： [1]Patent: WO2004/74255,2004,A2 .Location in patent: Page 89-90

15
[ 455-14-1 ]
[ 30414-53-0 ]
[ 749921-33-3 ]

Yield	Reaction Conditions	Operation in experiment
10.3%	With hydrogen In isopropyl alcohol at 80℃; for 15h;	24 [RuCl (p-cymene) ((R)-SEGPHOS)] Cl (17. 6 mg, 0.0192 mmol), methyl 3-oxopentanoate (500 mg, 3.842 mmol), 4-trifluoromethylaniline (619 mg, 3.842 mmol) and 2-propanol (2. 5 mL) were placed in a 2.5 mL-stainless autoclave under atmosphere of nitrogen, and the mixture was stirred under a hydrogen pressure of 3 MPa at 80°C for 15 hours. After completion of the reaction, the solvent was removed by evaporation in vacuo, and the residue was purified by column chromatography on silica gel (eluent: hexane ethyl acetate=3/1) to give methyl (3R)-3- (4-TRIFLUOROMETHYLPHENYLAMINO)- pentanoate (109 mg) as a colorless oil in 10. 3% yield. The enantiomeric excess of the product was found to be 92. 7% ee determined by HPLC analysis using a SUMICHIRAL OA-2500 column (available from SUMIKA CHEMICAL ANALYSIS SERVICE LTD.). LH-NMR (CDCL3) : B ; 0.97 (t, J=7.4Hz, 3H), 1.58-1. 68 (m, 2H), 2.55 (d, J =6. 1HZ, 2H), 3.66 (s, 3H), 3.77-3. 81 (m, LH), 4.13 (brs, LH), 6.62 (d, J =8.5Hz, 2H), 7.39 (d, J=11.4Hz, 2H).

Reference： [1]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - WO2005/28419, 2005, A2 Location in patent: Page/Page column 57

16
[ 30414-53-0 ]
[ 950-81-2 ]
[ 80880-62-2 ]
[ 533939-12-7 ]

Yield	Reaction Conditions	Operation in experiment
36%	With hydrogenchloride In methanol; n-heptane; 2,2,2-trifluoroethanol; ethyl acetate	5.1 Part 1 Part 1 2,6-Diethyl-pyridine-3,5-dicarboxylic acid dimethyl Ester A mixture of methyl-3-oxo-pentanoate (3.15 g, 24.2 mmol), methyl-3-amino-pentenoate (3.15 g, 24.3 mmol) and 4-antipyrinecarboxaldehyde (5.00 g, 23.1 mmol) in 2,2,2-trifluroethanol (4 mL) in a teflon screwcap glass pressure vessel is heated to 100° C. with stirring overnight. After cooling to room temperature, the contents of the vessel are transferred to a flask containing methanol (10 mL) and concentrated hydrochloric acid (4.0 mL, 48 mmoL), and the mixture is stirred at 90° C. for 6 h. The contents are poured into 50% aq NaHCO3 (100 mL), extracted with ethyl acetate (2*50 mL) and dried over Na2SO4. The crude material is purified by medium-pressure liquid chromatography (MPLC) on silica (5-50% ethyl acetate in heptane) to afford the product as a white solid (2.1 g, 36%); Rf 0.55 (30% ethyl acetate in heptane); 1H NMR (CDCl3, 300 MHz) δ8.64 (s, 1 H), 3.93 (s, 6 H), 3.20 (q, J=7.5 Hz, 4 H), 1.31 (t, J=7.5 Hz, 6 H); ESI-LCMS m/z calcd for C13H17NO4: 251.1; found 252.0 (M+1)+.

Reference： [1]Current Patent Assignee: INSTITUES FOR PHARMACEUTICAL D; INSTITUTE FOR DIABETES DISCOVERY; INSTITUTES FOR PHARMACEUTICAL DISCOVERY - US2003/166668, 2003, A1

17
[ 30414-53-0 ]
[ 20017-67-8 ]
(3,3-diphenylpropane-1-yl) 3-oxopentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;	1) Synthesis of (3,3-diphenylpropane-1-yl) 3-oxopentanoate: 3.0 g (23.1 mg) of methyl 3-oxopentanoate and 4.9 g (23.1 mg) of <strong>[20017-67-8]3,3-diphenylpropanol</strong> were stirred in 60 ml of toluene under heating at 100 C. overnight. Toluene was distilled out under reduced pressure to obtain the title compound. MS (ESI, m/z) 311 (M+H)+1H-NMR (CDCl3): 1.10 (3H, t), 2.32-2.45 (3H, m), 2.55 (1H, q), 3.40 (2H, s), 4.03-4.12 (3H, m), 7.16-7.31 (10H, m)

Reference： [1]Patent: US2002/147222,2002,A1

18
[ 30414-53-0 ]
[ 79-03-8 ]
[ 158511-22-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; magnesium chloride In dichloromethane at 2 - 20℃; for 1h;	1.A 5.21 g=5.02 ml (39.2 mmol) of 3-oxo-pentanoic acid methyl ester were dissolved in 30 ml of CH2Cl2, the solution was cooled to 2° C. and 3.81 g (39.2 mmol) of anhydrous magnesium chloride were added in small portions. Then, 6.21 g=6.34 ml (78.4 mmol) of pyridine were added to this suspension between 2° C. and 5° C., followed by 3.89 g=3.67 ml (41.2 mmol) of propionyl chloride. The reaction mixture was warmed up to RT and 1 hour later poured into crashed ice, acidified with HCl (25%) to pH 1-2 and extracted twice with Et2O. The organic phases were dried over magnesium sulfate, filtered and evaporated to give 7.62 g of title compound as light yellow oil. MS: 185.1 ([M-H]-).
	With calcium hydroxide In tert-butyl methyl ether	1a Process description, Step la, compound B: Compound A and MTBE were mixed and calcium hydroxide and propionylchloride was added. The reaction was cooled and aqueous HCI was added. The reaction was worked up using NaHC03. The organic layer was concentrated under vacuum to afford compound B as an oil.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2009/29963, 2009, A1 Location in patent: Page/Page column 11
[2]Current Patent Assignee: LEO FONDET - WO2017/108927, 2017, A1 Location in patent: Page/Page column 6

19
[ 30414-53-0 ]
[ 3222-61-5 ]
[ 61268-05-1 ]
[ 1151643-07-0 ]

Yield	Reaction Conditions	Operation in experiment
64%	In ethanol for 14h; Reflux;

Reference： [1]Location in patent: experimental part Fawzy [Heterocyclic Communications, 2008, vol. 14, # 3, p. 169 - 182]

20
[ 30414-53-0 ]
[ 1903-91-9 ]
[ 911388-92-6 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of 2-methoxymethyl-4-hydroxy-6-ethylpyrimidine; 116 ml of a 30% strength sodium methoxide solution are diluted with 100 ml of methanol and, with ice-cooling, a solution of 26 g (208.7 mmol) of methoxy-acetamidinium hydrochloride in 200 ml of methanol is added dropwise. After the dropwise addition, the mixture is stirred for 1 h, and a solution of 27.1 g (208.7 mmol) of methyl propionyl acetate in 100 ml of methanol is then added dropwise at RT. The reaction mixture is stirred at RT for 96 h. For work-up, the reaction mixture is concentrated, the residue is taken up in 100 ml of H2O and the aqueous mixture is adjusted to pH 6 using concentrated HCl. The mixture is then concentrated and the residue is taken up in 30 ml of methanol. The solid is filtered off with suction, and concentration of the mother liquor gives 38.5 g of product. 1H-NMR: delta [CDCl3] 1.20 (t, 3H), 2.50 (q, 2H), 3.42 (s, 3H), 4.35 (s, 2H), 6.04 (s, 1H).

Reference： [1]Patent: US2006/223708,2006,A1 .Location in patent: Page/Page column 10

21
[ 30414-53-0 ]
[ 4946-13-8 ]
[ 1190220-10-0 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentoxide In dichloromethane at 20℃; for 18h;

Reference： [1]Location in patent: scheme or table Iqbal, Inam; Imran, Muhammad; Rasool, Nasir; Rashid, Muhammad A.; Hussain, Munawar; Villinger, Alexander; Fischer, Christine; Langer, Peter [Tetrahedron, 2009, vol. 65, # 36, p. 7562 - 7572]

22
[ 30414-53-0 ]
[ 42558-50-9 ]
[ 62-53-3 ]
methyl (R)-3-(phenylamino)valerate [ No CAS ]
[ 774216-22-7 ]

Yield	Reaction Conditions	Operation in experiment
85%		<Example 5> To a solution of 6.22 mg (48 mmol) of methyl 3-ketovalerate in 48 ml methanol, 36 mg (0.004 mmol) RuCl2(S)-binap was added and stirred in an autoclave under a hydrogen pressure of 30 atm at 80 C for 66 hours. After concentration and distillation, 5.71 g (43.2 mmol, 97%ee) of <strong>[42558-50-9]methyl (S)-3-hydroxyvalerate</strong> was obtained. The condition of chiral HPLC is the following. Column, CHIRALPAK OD manufactured by Daicel Chemical Industries, Ltd.; Eluate, Hexane:2-propanol=95:5; flow rate, 1.0mL/min; Wavelength of detection, 210nm; Temperature, 25C; Retention time, 15min (R) and 27min (S). A solution of 270 mg (2.0 mmol, 97%ee) of this methyl (S)-3-hydroxybutanoate and 0.38 ml (2.2 mmol) of diisopropylamine in 2 ml of dichloromethane was cooled to -78 C and a solution of 634 mg (2.3 mmol) trifluoromethanesulfonic acid anhydride in 2 ml of dichloromethane was added by dropping within 1 hour under stirring. After cooling the mixture to -78 C, 0.56 ml (6.1 mmol) of aniline was added and stirred at -40 C for 16 hours. After quenching with trifluoroacetic acid, the yield and optical purity of methyl (R)-3-(phenylamino)valerate were determined by HPLC (yield 85%, optical purity 97% ee). The condition of chiral HPLC is the following. Column, CHIRALPAK AS-H manufactured by Daicel Chemical Industries, Ltd.; Eluate, Hexane:2-propanol=95:5; flow rate, 1.0mL/min; Wavelength of detection, 210nm; Temperature, 25C; Retention time, 6.1min (R) and 6.8min (S).1H-NMR (400 MHz, CDCl3): δ 0.98 (t, J= 7.4 Hz, 3H), 1.54-1.70 (m, 2H), 2.49 (dd, J = 15.0, 6.3 Hz, 1H), 2.58 (dd, J = 15.0, 5.7 Hz, 1H), 3.66 (s, 3H), 3.72-3.78 (m, 1H), 6.61-6.64 (m, 2H), 6.67-6.71 (m, 1H), 7.14-7.19 (m, 2H);13C-NMR (100MHz, CDCl3): δ 10.88, 28.14, 39.12, 52.00, 52.23, 113.89, 117.92, 129.74, 147.57, 172.83; IR (neat) 3390, 2970, 1729, 1602, 1507 cm-1; ESIMS m/z: 208 (M+H); Elemental analysis: calcd. for C12H17NO2: C, 69.54; H, 8.27; N, 6.76; found: C, 69.48; H, 8.31; N, 6.50; [α]23D= +27.6 (c = 2.1, CH2Cl2).

Reference： [1]Patent: EP1471050,2004,A1 .Location in patent: Page 8; 9

23
[ 30414-53-0 ]
[ 1193-24-4 ]
[ 929902-90-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 171 - 176

24
[ 30414-53-0 ]
[ 672-47-9 ]
[ 1260235-94-6 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 171 - 176

25
[ 30414-53-0 ]
[ 16883-69-5 ]
[ 1571-08-0 ]
methyl trans-5-benzoyl-2-ethyl-4-(p-methoxycarbonylphenyl)-4,5-dihydrofuran-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With piperidine In acetonitrile at 60℃; for 14h; stereoselective reaction;	Typical procedure for the one-pot reaction in acetonitrile: General procedure: A solution of 2,4-pentanedione (4A, 210 mg, 2.10 mmol), benzaldehyde (5a, 339 mg, 3.20 mmol), N-phenacylpyridinium bromide (2a, 875 mg, 3.15 mmol), and piperidine (701 mg, 8.45 mol) in acetonitrile (10 mL) was stirred at 60 °C for 14 h. The reaction mixture was diluted with ethyl acetate (100 mL), washed with water (3×50 mL), and dried (Na2SO4). The solvent was evaporated under reduced pressure and the residue was chromatographed over silica gel (20 g), using hexane-ethyl acetate (8:1) as eluent, followed by recrystallization (hexane-ethyl acetate) to give 3a (526 mg, 82%).

Reference： [1]Location in patent: experimental part Chuang, Che-Ping; Chen, Kuang-Po [Tetrahedron, 2012, vol. 68, # 5, p. 1401 - 1406]

26
[ 30414-53-0 ]
[ 948592-80-1 ]
[ 1423076-84-9 ]

Reference： [1]Synthesis,2012,vol. 44,p. 3811 - 3814

27
[ 30414-53-0 ]
[ 863578-36-3 ]
[ 1423076-86-1 ]

Yield	Reaction Conditions	Operation in experiment
38%	With potassium chloride; oxygen; copper diacetate In methanol at 50℃;

Reference： [1]Bunescu, Ala; Wang, Qian; Zhu, Jieping [Synthesis, 2012, vol. 44, # 24, p. 3811 - 3814]

28
[ 30414-53-0 ]
[ 33403-97-3 ]
[ 1400304-34-8 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 8038 - 8048

29
[ 30414-53-0 ]
[ 33403-97-3 ]
[ 1400304-26-8 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 8038 - 8048

30
[ 30414-53-0 ]
[ 3952-66-7 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 7268 - 7273

31
[ 30414-53-0 ]
[ 428854-24-4 ]
[ 1361569-69-8 ]

Yield	Reaction Conditions	Operation in experiment
25%	In ethanol; for 48h;Reflux;	Example 94 4-Amino-6-ethyl-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pteridin-7(8H)-one 250 mg (0.714 mmol) of the compound from example 1A were initially charged in ethanol (3.8 ml), then 102 mg (0.785 mmol) of methyl 3-oxopentanoate were added and the reaction mixture was heated to reflux for two days. The reaction mixture was brought to RT and filtered. The solids were washed with ethanol, then suspended in dimethylformamide, and the mixture was left to stand overnight. Thereafter, the supernatant solution was decanted and discarded. The remaining residue was stirred repeatedly with methanol and the supernatant solution was discarded each time. The residue was dried under high vacuum and, after lyophilization, 77 mg (25% of theory) of the title compound were obtained in solid form. LC-MS (method 2): Rt=0.96 min MS (ESIpos): m/z=417 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta=1.24 (t, 3H), 2.76 (q, 2H), 5.84 (s, 2H), 7.12-7.28 (m, 3H), 7.32-7.47 (m, 3H), 7.89 (br. s, 1H), 8.63-8.68 (m, 1H), 9.14-9.20 (m, 1H), 12.72 (s, 1H).

Reference： [1]Patent: US2014/148433,2014,A1 .Location in patent: Paragraph 1437; 1438; 1439; 1440

32
[ 30414-53-0 ]
[ 1122-85-6 ]
methyl 3-hydroxy-2-(imino(phenoxy)methyl)pent-2-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	In toluene; at 20℃; for 40h;	In step (1) to PhenoxyNitrile,Ethyl acetoacetate as raw material,Ether as solvent,According to phenylene oxide millimolar:Acetoacetate B (129.8 muL, 1.2 mmol), ethyl acetoacetate (127.6 muL, 1.0 mmol) and diethyl ether (2.0 mL) were added to the reactor in the reactor at a ratio of 1.2: 1: ), The addition is complete, stirring at room temperature Reaction for 40 hours.(2) After completion of step (1), the reaction solution of the imidate derivative prepared in step (1) is subjected to rotary evaporation The concentrate was collected by silica gel column chromatography and eluted with eluent. The eluate was purified by silica gel column chromatography Concentrated by rotary evaporation and dried to give white solid imidate 3a (214 mg, yield 86%).The eluent is a mixture of ethyl acetate: petroleum ether in a volume ratio of 1: (2 to 20).
46%	With pyrrole; In diethyl ether; at 20℃; for 40h;	General procedure: Compounds 2a-i were synthesized according to the reported method: a mixture of ethyl acetoacetate (6 mmol), <strong>[1122-85-6]phenyl cyanate</strong> (5 mmol) in diethyl ether (10 mL) at room temperature for 40 h. After completion of the reaction monitored by TLC, the volatile components were removed using a vacuum rotary evaporator. Purification by column chromatography on silica gel produced 3-hydroxybut-2-enimidates 2a-i.

Reference： [1]Patent: CN105017077,2017,B .Location in patent: Paragraph 0024-0029; 0070-0074; 0075-0094; 0097; 0098
[2]Chinese Chemical Letters,2014,vol. 25,p. 1327 - 1330
[3]Tetrahedron,2016,vol. 72,p. 5749 - 5753

33
[ 30414-53-0 ]
[ 99662-34-7 ]
methyl 2-(4-(1H-pyrazol-1-yl)benzylidene)-3-oxopentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; acetic acid; In benzene; at 90℃; for 4h;Dean-Stark;	A mixture containing methyl 3-oxopentanoate (2.2 g, 17 mmol), <strong>[99662-34-7]4-(1H-pyrazol-1-yl)benzaldehyde</strong> (2.5 g, 14 mmol), piperidine (0.3 mL, 3.0 mmol), and acetic acid (0.16 mL, 2.8 mmol) in benzene (70 mL) was heated to 90 C. with removal of water (Dean-Stark trap). After 4 hours, the mixture was cooled to 23 C. and then concentrated to provide the title compound.
	With piperidine; acetic acid; In benzene; at 90℃; for 4h;Dean-Stark;	Intermediate 32: step a methyl 2-(4-(1H-pyrazol-1-yl)benzylidene)-3-oxopentanoate A. mixture containing methyl 3-oxopentanoate (2.2 g, 17 nimol), 4-(lH-pyrazol-l - yl)benzaldehyde (2.5 g, 14 mmol), piperidine (0.3 mL, 3.0 mmol), and acetic acid (0.16 mL, 2.8 mmol) in benzene (70 mL) was heated to 90 C with removal of water (Dean-Stark trap). After 4 hours, the mixture was cooled to 23 C and then concentrated to provide the title compound. The residue (mixture of alkene isomers) was taken onto the next step without further purification.

Reference： [1]Patent: US2015/105366,2015,A1 .Location in patent: Paragraph 0352; 0353
[2]Patent: WO2015/57205,2015,A1 .Location in patent: Page/Page column 101; 102

34
[ 30414-53-0 ]
[ 211308-81-5 ]
C₁₁H₁₁ClN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With copper(l) iodide; caesium carbonate; 1,1'-bi-2-naphthol; In dimethyl sulfoxide; for 15h;Inert atmosphere;	Preparation of intermediate CD A mixture of <strong>[211308-81-5]5-chloro-3-iodopyridin-2-amine</strong> (CAS [211308-81-5], 4 g, 15.72 mmol), 2,4-Hexadione (CAS [3002-24-2], 4.50 g, 34.58 mmol), cesium carbonate (5.12 g, 15.71 mmol), BINOL (900.20 mg, 3.14 mmol) and copper iodide (299.39 mg, 1.57 mmol) in DMSO (50 mL) was stirred for 15 hours under N2 flow. Brine and ethyl acetate were added to the mixture. The organic layer was separated, washed with brine, dried over MgS04 and filtered. The filtrate was concentrated. The crude product was purified by column chromatography over silica gel (eluent: ethyl acetate/hexane from 0 to 1/1). The desired fractions were collected and concentrated to give intermediate CD, 2.5 g, 67%

Reference： [1]Patent: WO2017/1660,2017,A1 .Location in patent: Page/Page column 97

35
[ 30414-53-0 ]
[ 106-96-7 ]
[ 100330-50-5 ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 3481 - 3484

36
[ 247037-82-7 ]
[ 30414-53-0 ]
[ 84194-36-5 ]
[ 247037-77-0 ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 969 - 974

37
[ 41340-36-7 ]
[ 30414-53-0 ]
methyl 1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)-indole-1-acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99.9%	With chloro-trimethyl-silane In methanol at 20℃; for 22h;	1-4 Add 96.4 g of 7-ethylchromanol (content 98.0%, equivalent to 0.5 mol), 68.3 g (0.525 mol) of methyl 3-oxopentanoate, and add trimethyl chloride to the constant pressure dropping funnel. 57.0 g (0.525 mol) of silane, and slowly added dropwise to the above reaction system, controlling the temperature not to exceed 20°C, the dropping time is about 4 hours, and the reaction is completed at 20°C overnight (about 18 hours) to 7-ethyl color The HPLC content of alcohol is less than 0.1%, cooled to 10 , and kept for 1 hour, filtered, rinsed with 25 grams of cold methanol, the mother liquor to be treated.The filtrate was rinsed with 150 g of 5% sodium bicarbonate solution and 50 g of water, and dried to obtain a white solid product: 150.3 g, HPLC purity: 99.78%, yield: 99.9%
98%	With sulfuric acid In methanol at 0 - 30℃;

Reference： [1]Current Patent Assignee: ZHEJIANG INTERNATIONAL STUDIES UNIV - CN111303172, 2020, A Location in patent: Paragraph 0050-0087
[2]Habinovec, Iva; Car, Zeljka; Ribic, Rosana; Galic, Nives; Novak, Predrag; Mestrovic, Ernest; Tomic, Srdanka [Croatica Chemica Acta, 2016, vol. 89, # 4]

38
[ 41340-36-7 ]
[ 30414-53-0 ]
[ 41340-25-4 ]

Reference： [1]Croatica Chemica Acta,2016,vol. 89

39
[ 30414-53-0 ]
[ 115955-48-1 ]
methyl 6-(3-nitrophenyl)-2-ethyl-nicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.55 g	With cerium(III) chloride heptahydrate; ammonium acetate; sodium iodide; In isopropyl alcohol;Reflux;	6.31 g of 3-dimethylamino-1-(3-nitro-phenyl)-prop-2-en-1-one (28.7 mmol, 1 equiv.), 4.47 g of methyl propionylacetate (34.4 mmol, 1.2 equiv.), 4.42 g of ammonium acetate (57.4 mmol, 2.0 equiv.), 2.14 g of cerium(III) chloride heptahydrate (5.7 mmol, 0.2 equiv.), 860 mg of sodium iodide (5.7 mmol, 0.2 equiv.) and 35 ml of isopropanol were mixed and refluxed overnight under stirring. The reaction solution was cooled and filtered, and the filtrate was concentrated and subjected to column chromatography, eluting with ethyl acetate/petroleum ether (1:50) to obtain 1.55 g of methyl 6-(3-nitro-phenyl)-2-ethyl-nicotinate as a yellow solid.

Reference： [1]Patent: EP3287456,2018,A1 .Location in patent: Paragraph 0155

40
[ 115933-37-4 ]
[ 30414-53-0 ]
methyl 6-(4-tert-butylphenyl)-2-ethyl-nicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53.4%	With cerium(III) chloride heptahydrate; ammonium acetate; sodium iodide In isopropyl alcohol Reflux;	5.2 Step 2: Preparation of methyl 6-(4-tert-butyl-phenyl)-2-ethyl-nicotinate 3.0 g of 1-(4-tert-butyl-phenyl)-3-dimethylamino-prop-2-en-1-one (12.9 mmol, 1.0 equiv.), 2.0 g of methyl propionylacetate (15.4 mmol, 1.2 equiv.), 2.0 g of ammonium acetate (25.8 mmol, 2.0 equiv.), 483 mg of cerium(III) chloride heptahydrate (1.29 mmol, 0.2 equiv.), 194 mg of sodium iodide (1.29 mmol, 0.2 equiv.) and 30 ml of isopropanol were mixed and refluxed overnight under stirring. The reaction solution was cooled and filtered, and the filtrate was concentrated and subjected to column chromatography, eluting with ethyl acetate/petroleum ether (1:50) to obtain 2.0 g of methyl 6-(4-tert-butyl-phenyl)-2-ethyl-nicotinate as a yellow liquid, 52.2%.

Reference： [1]Current Patent Assignee: 3SBIO INC. - EP3287456, 2018, A1 Location in patent: Paragraph 0064

41
[ 30414-53-0 ]
[ 55314-16-4 ]
methyl 6-ethyl-[2,3']bipyridyl-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61.9%	With cerium(III) chloride heptahydrate; ammonium acetate; sodium iodide; In isopropyl alcohol;Reflux;	4.83 g of 3-dimethylamino-1-pyridin-3-yl-prop-2-en-1-one (30.0 mmol, 1.0 equiv), 4.68 g of methyl propionylacetate (36.0 mmol, 1.2 equiv.), 4.62 g of ammonium acetate (60.0 mmol, 0.2 equiv.), 2.25 g of cerium (III) chloride heptahydrate (6.0 mmol, 0.2 equiv.), 900 mg of sodium iodide (6.0 mmol, 0.2 equiv.) and 30 ml of isopropanol were mixed and refluxed overnight under stirring. The reaction solution was cooled and filtered, and the filtrate was concentrated and subjected to column chromatography, eluting with ethyl acetate/petroleum ether (1:50) to obtain 4.5 g of methyl 6-ethyl- [2,3'] bipyridyl-5-carboxylate as a yellow solid, 61.9%.

Reference： [1]Patent: EP3287456,2018,A1 .Location in patent: Paragraph 0071

42
[ 30414-53-0 ]
[ 163852-04-8 ]
methyl 6-(3-bromophenyl)-2-ethyl-nicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60.4%	With cerium(III) chloride heptahydrate; ammonium acetate; sodium iodide; In isopropyl alcohol;Reflux;	4.2 g of 1-(3-bromo-phenyl)-3-dimethylamino-prop-2-en-1-one (20.1 mmol, 1.0 equiv.), 2.75 g of methyl propionylacetate (24.1 mmol, 1.2 equiv.), 3.1 g of ammonium acetate (40.2 mmol, 2.0 equiv.), 1.51 g of cerium(III) chloride heptahydrate (4.02 mmol, 0.2 equiv.), 603 mg of sodium iodide (4.02 mmol, 0.2 equiv.) and 40 ml of isopropanol were mixed and refluxed overnight under stirring. The reaction solution was cooled and filtered, and the filtrate was concentrated and subjected to column chromatography, eluting with ethyl acetate/petroleum ether (1:50) to obtain 3.7 g of methyl 6-(3-bromo-phenyl)-2-ethyl-nicotinate as a yellow liquid, 60.4%.

Reference： [1]Patent: EP3287456,2018,A1 .Location in patent: Paragraph 0092

43
[ 30414-53-0 ]
[ 259654-73-4 ]

Reference： [1]Patent: US2018/153860,2018,A1

44
[ 30414-53-0 ]
[ 496062-15-8 ]

Reference： [1]Patent: US2018/153859,2018,A1
[2]Patent: US2018/153860,2018,A1

45
[ 30414-53-0 ]
[ 496062-16-9 ]

Reference： [1]Patent: US2018/153859,2018,A1
[2]Patent: US2018/153860,2018,A1

46
[ 6728-26-3 ]
[ 30414-53-0 ]
2-methyl-5-n-propylcyclohex-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With sodium hydroxide In ethanol; water at 0℃; for 1h; Reflux;	32 Example 1.2: Synthesis of 6-Ethyl-4-isopropylcyclohex-2-en-1-one (1) At 0° C., ethyl-2-ethyl acetoacetate (17.5 g, 0.11 mol) in ethanol (25 ml) is added dropwise to 50% aqueous NaOH (8.8 g, 0.11 mol) in ethanol (90 ml), then 3-methyl-2-methylenebutanal (10.3 g, 0.11 mol) in ethanol (25 ml) is added dropwise. The reaction mixture is heated under reflux for 1 hour and the solvent is subsequently distilled off. Water (170 ml) and MtBE (150 ml) are added to the reaction mixture and the phases are separated. The organic phase is neutralized with 50% aqueous sulfuric acid (8.8 g), dried over sodium sulfate and concentrated in a vacuum. Column chromatographic purification on silica gel (eluent: cyclohexane/acetic acid ethyl ester 40/1) gives 6-ethyl-4-isopropylcyclohex-2-en-1-one as an isomer mixture in the form of a colorless oil (2.8 g, 17%).

Reference： [1]Current Patent Assignee: SYMRISE AG - US10045551, 2018, B2 Location in patent: Paragraph 45; 56

47
[ 30414-53-0 ]
[ 146948-68-7 ]
methyl 5-chloro-2-ethyl-7-methyl-1H-indole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With copper(l) iodide; 1H-tetrazol-1-ylacetic acid; caesium carbonate In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere; Sealed tube;	1-1.1 Step 1: Methyl 5-chloro-2-ethyl-7-methyl-l//-indole-3-carboxylate Cesium carbonate (8.87 g, 27.2 mmol), 2-( H- .2.3.4- tetraa/ol- 1 -yl /acetic acid (Apollo Scientific Ltd., 0.35 g, 2.72 mmol), copper(I) iodide (0.26 g, 1.36 mmol) and 2-bromo-4-chloro-6- methylaniline (3.00 g, 13.6 mmol) were weighed into a 50-mL vial. The solids were purged with argon, treated with DMSO (15 mL) and methyl 3-oxopentanoate (6.83 mL, 54.4 mmol) and the vial sealed and heated to 80 °C for 24 h. The reaction mixture was cooled to rt, treated with water and extracted with EtOAc, washed with brine and dried over MgS04, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (eluent: 0-40% EtO Ac/heptane) affording methyl 5-chloro-2-ethyl-7-methyl- l//-indole-3-carboylate (2.39 g, 9.50 mmol, 70 %yield) as a light yellow crystalline solid. 1H NMR (400 MHz, DMSO- ck) d ppm 11.82 (1 H, br s), 7.72 (1 H, s), 6.99 (1 H, s), 3.82 (3 H, s), 3.09 (2 H, q, J= 7.5 Hz), 2.46 - 2.47 (3 H, m), 1.26 (3 H, t, J= 7.5 Hz) m/z (ESI, +ve ion): 252.1 (M+H)+.

Reference： [1]Current Patent Assignee: AMGEN INC - WO2020/106640, 2020, A1 Location in patent: Paragraph 0195

48
[ 30414-53-0 ]
[ 5202-85-7 ]
Methyl 2-(6-chloro-2-ethyl-4-oxo-1,2,3,4-tetrahydroquinazolin-2-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With α-chymotrypsin In ethanol at 60℃; for 40h; Enzymatic reaction;	Path B: General procedure: A 10-mL stoppered bottle was filled with the required 2-aminobenzamide (0.2 mmol), dicarbonyl compound (0.6 mmol), α-chymotrypsin (2400U), 2 mL EtOH and oscillate in a constant temperature shaker at 60 °C for 40 h.

Reference： [1]Gong, Bozhen; Lan, Jin; Le, Zhanggao; Li, Hongxia; Meng, Jia; Xie, Zongbo [Molecular catalysis, 2020, vol. 498]

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Code	Phrase
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 30414-53-0 ]

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Safety of [ 30414-53-0 ]

Application In Synthesis of [ 30414-53-0 ]

[ 30414-53-0 ] Synthesis Path-Upstream 1~32

[ 30414-53-0 ] Synthesis Path-Downstream 1~48

Related Functional Groups of [ 30414-53-0 ]

Aliphatic Chain Hydrocarbons

Esters

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 30414-53-0 ]