[ CAS No. 23462-75-1 ] {[proInfo.proName]}

Name: 23462-75-1|Dihydro-2H-pyran-3(4H)-one|95%
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Quality Control of [ 23462-75-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 23462-75-1 ]

CAS No. :	23462-75-1	MDL No. :	MFCD00182426
Formula :	C₅H₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	URUUZIAJVSGYRC-UHFFFAOYSA-N
M.W :	100.12	Pubchem ID :	90109
Synonyms :

Calculated chemistry of [ 23462-75-1 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	25.32
TPSA :	26.3 Å²

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) :	-6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.31
Log Po/w (XLOGP3) :	-0.01
Log Po/w (WLOGP) :	0.37
Log Po/w (MLOGP) :	-0.31
Log Po/w (SILICOS-IT) :	1.64
Consensus Log Po/w :	0.6

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.45
Solubility :	35.2 mg/ml ; 0.351 mol/l
Class :	Very soluble
Log S (Ali) :	-0.09
Solubility :	80.8 mg/ml ; 0.807 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.82
Solubility :	15.2 mg/ml ; 0.152 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.44

Safety of [ 23462-75-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 23462-75-1 ]

* 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 [ 23462-75-1 ]
Downstream synthetic route of [ 23462-75-1 ]

[ 23462-75-1 ] Synthesis Path-Upstream 1~15

1
[ 67-56-1 ]
[ 78870-52-7 ]
[ 29943-42-8 ]
[ 23462-75-1 ]

Reference： [1] Tetrahedron, 2003, vol. 59, # 9, p. 1453 - 1467

2
[ 23462-75-1 ]
[ 873397-34-3 ]

Reference： [1] Heterocycles, 2011, vol. 82, # 2, p. 1267 - 1282

3
[ 19752-84-2 ]
[ 23462-75-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium acetate; sode de l'acide trichloroisocyanurique In dichloromethane at 25℃; for 2 h;	Compound 2 (300 g, 2.9 mol) was dissolved in 3000 g of dichloromethane and sodium acetate (287 g, 3.5 mol) was added.TEMPO 6g, add sodium dichloroisocyanurate (374g, 1.7mol) in batch at 25°C, maintain the reaction at 25°C for 2h, filter,The organic phase was dried with 200g of anhydrous sodium sulfate, filtered and concentrated in a water pump and distilled to collect the oil temperature of 120°C and the top temperature of 90°C.250 g of a colorless oily liquid having a purity of 99percent and a yield of 83percent.
32.4%	With pyridinium chlorochromate In dichloromethane at 20℃;	To PCC (10.35 g, 48 mmol)Tetrahydro-2H-pyran-3-ol (3.27 g, 32 mmol) was added to a solution of dichloromethane (100 mL).The reaction was stirred overnight at room temperature and partially concentrated.The residue was diluted with ethyl acetate (100 mL) and filtered over celite.The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography on silica gel (PE/EtOAc (v/v) = 2/1).The title compound was obtained as a colorless oil (1.037 g, 32.4percent).

Reference： [1] Heterocycles, 2011, vol. 82, # 2, p. 1267 - 1282
[2] Patent: CN107382928, 2017, A, . Location in patent: Paragraph 0007-0008; 0010-0011; 0013-0014
[3] Liebigs Annalen der Chemie, 1983, # 11, p. 1950 - 1958
[4] Tetrahedron, 2003, vol. 59, # 9, p. 1453 - 1467
[5] Patent: CN104650049, 2018, B, . Location in patent: Paragraph 0603; 0604
[6] Canadian Journal of Chemistry, 1983, vol. 61, p. 1924 - 1932
[7] Tetrahedron, 2004, vol. 60, # 46 SPEC. ISS., p. 10411 - 10418
[8] Patent: WO2009/85256, 2009, A1, . Location in patent: Page/Page column 70-71
[9] Patent: US2009/259049, 2009, A1, . Location in patent: Page/Page column 10-11
[10] Patent: WO2010/57121, 2010, A1, . Location in patent: Page/Page column 156
[11] Patent: US2010/160280, 2010, A1, . Location in patent: Page/Page column 133; 134
[12] Patent: US2011/86882, 2011, A1, . Location in patent: Page/Page column 21

4
[ 98166-23-5 ]
[ 23462-75-1 ]

Reference： [1] Archiv der Pharmazie, 1985, vol. 318, # 6, p. 548 - 555

5
[ 1403495-64-6 ]
[ 23462-75-1 ]

Reference： [1] Arkivoc, 2012, vol. 2012, # 8, p. 226 - 230

6
[ 98166-29-1 ]
[ 23462-75-1 ]

Reference： [1] Archiv der Pharmazie, 1985, vol. 318, # 6, p. 548 - 555

7
[ 78870-52-7 ]
[ 23462-75-1 ]

Reference： [1] Tetrahedron, 2003, vol. 59, # 9, p. 1453 - 1467

8
[ 110-87-2 ]
[ 23462-75-1 ]

Reference： [1] Heterocycles, 2011, vol. 82, # 2, p. 1267 - 1282
[2] Patent: CN104650049, 2018, B,

9
[ 4469-60-7 ]
[ 23462-75-1 ]

Reference： [1] Arkivoc, 2012, vol. 2012, # 8, p. 226 - 230

10
[ 328-50-7 ]
[ 23462-75-1 ]

Reference： [1] Arkivoc, 2012, vol. 2012, # 8, p. 226 - 230

11
[ 73819-79-1 ]
[ 542-28-9 ]
[ 23462-75-1 ]
[ 73819-79-1 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 45 - 48

12
[ 73819-79-1 ]
[ 542-28-9 ]
[ 23462-75-1 ]
[ 73819-79-1 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 45 - 48

13
[ 67-56-1 ]
[ 78870-52-7 ]
[ 29943-42-8 ]
[ 23462-75-1 ]

Reference： [1] Tetrahedron, 2003, vol. 59, # 9, p. 1453 - 1467

14
[ 23462-75-1 ]
[ 73183-34-3 ]
[ 212127-81-6 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 7, p. 666 - 670

15
[ 23462-75-1 ]
[ 212127-81-6 ]

Reference： [1] Patent: WO2016/89797, 2016, A1,
[2] Patent: WO2017/176961, 2017, A1,

[ 23462-75-1 ] Synthesis Path-Downstream 1~16

1
[ 19752-84-2 ]
[ 23462-75-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium acetate; sode de l'acide trichloroisocyanurique; In dichloromethane; at 25℃; for 2h;	Compound 2 (300 g, 2.9 mol) was dissolved in 3000 g of dichloromethane and sodium acetate (287 g, 3.5 mol) was added.TEMPO 6g, add sodium dichloroisocyanurate (374g, 1.7mol) in batch at 25C, maintain the reaction at 25C for 2h, filter,The organic phase was dried with 200g of anhydrous sodium sulfate, filtered and concentrated in a water pump and distilled to collect the oil temperature of 120C and the top temperature of 90C.250 g of a colorless oily liquid having a purity of 99% and a yield of 83%.
32.4%	With pyridinium chlorochromate; In dichloromethane; at 20℃;	To PCC (10.35 g, 48 mmol)Tetrahydro-2H-pyran-3-ol (3.27 g, 32 mmol) was added to a solution of dichloromethane (100 mL).The reaction was stirred overnight at room temperature and partially concentrated.The residue was diluted with ethyl acetate (100 mL) and filtered over celite.The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography on silica gel (PE/EtOAc (v/v) = 2/1).The title compound was obtained as a colorless oil (1.037 g, 32.4%).
	With Dess-Martin periodane; In dichloromethane; for 1.33333h;Molecular sieve;	Oxidation of alcohol 49 (2.12 g, 20.8 mmol) with DMP (9.91 g, 23.3 mmol) in accordance with Method Y provides the pyranone 50 (1.78 g): 1H NMR (250 MHz, CDCl3, deltaH) 4.03 (s, 2H), 3.86 (app t, 2H), 2.54 (app t, 2H), 2.12 (m, 2H).; Method Y[0277] To a suspension of the 3-pyranol (1 equiv) and 4 A molecular sieves (2 g/g 3- pyranol) in DCM (5 mL/mmol) is added DMP (1 equiv) portionwise over 20 min. Reaction progress is monitored by TLC. Additional DMP (0.2 equiv) is added as required. After 1 h, the reaction mixture is partitioned between DCM and 2 M K2CO3. The organic phase is separated and the aqueous extracted with DCM (3 x). The combined organic phases are washed with brine, dried (MgSO4), filtered, and coned in vacuo. Column chromatography (silica gel, 1:2 EtOAc in heptanes) provides the 3-pyranones.

		To a mixture of oxalyl chloride (2.28 mL, 26.6 mmol) and dichloromethane (40 mL) was added a mixture of DMSO (3.78 mL, 53.2 mmol) and dichloromethane (20 mL) while stirring at -78 C., and the mixture was stirred at -78 C. for 30 minutes. After then adding to this mixture a mixture of tetrahydropyran-3-ol (synthesised according to the method described in Tetrahedron, 60, 10411-10418, 2004) (1.36 g, 13.3 mmol) and dichloromethane (20 mL) at -78 C., the resulting mixture was stirred at -78 C. for 30 minutes, after which triethylamine (11.1 mL, 79.8 mmol) was added and stirring was continued for 2 hours while slowly raising the temperature to 0 C. Brine and diethyl ether were added to the mixture, and after sufficient shaking, the organic layer was separated and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was then filtered, and the solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (1.62 g, 16.2 mmol). 1H-NMR(CDCl3) delta: 2.07-2.14 (m, 2H), 2.54 (t, J=6.8 Hz, 2H), 3.82-3.88 (m, 2H), 4.03 (s, 2H).
	With pyridinium chlorochromate; In dichloromethane; for 3h;Molecular sieve; Reflux;	To a stirred mixture ofpyridinium chlorochromate (11.02 g, 51.1 mmol) and 3 A molecular sieves (10.00 g) in DCM (100 mL) was added a solution of <strong>[19752-84-2]tetrahydro-2H-pyran-3-ol</strong> (3.48 g, 34.1 mmol) in DCM (100 mL). The reaction mixture was refluxed for 3 h before being cooled to room temperature and partially concentrated in vacuo. The mixture was then diluted with EtOAc and filtered through Celite. The filtrate was concentrated in vacuo and purified by silica gel chromatography to give dihydro-2H-pyran-3(4H)-one.
	With pyridinium chlorochromate; In dichloromethane; for 3h;Molecular sieve; Reflux;	STEP 2. DIHYDRO-2H-PYRAN-3(4H)-ONE To a stirred mixture of pyridinium chlorochromate (11.02 g, 51.1 mmol) and 3 A molecular sieves (10.0 g) in DCM (100 mL) was added a solution of <strong>[19752-84-2]tetrahydro-2H-pyran-3-ol</strong> (3.48 g, 34.1 mmol) in DCM (100 mL). The reaction mixture was refluxed for 3 h before being cooled to room temperature and partially concentrated in vacuo. The mixture was then diluted with EtOAc and filtered through Celite. The filtrate was concentrated in vacuo and purified by silica gel chromatography to give dihydro-2H-pyran-3(4H)-one.
		Production Example 1Dihydro-2H-pyran-3(4H)-one To a mixture of oxalyl chloride (2.28 mL, 26.6 mmol) and dichloromethane (40 mL) was added a mixture of DMSO (3.78 mL, 53.2 mmol) and dichloromethane (20 mL) while stirring at -78 C., and the mixture was stirred at -78 C. for 30 minutes. After then adding to this mixture a mixture of tetrahydropyran-3-ol (synthesized according to the method described in Tetrahedron, 60, 10411-10418, 2004) (136 g, 13.3 mmol) and dichloromethane (20 mL) at -78 C., the resulting mixture was stirred at -78 C. for 30 minutes, after which triethylamine (11.1 mL, 79.8 mmol) was added and stirring was continued for 2 hours while slowly raising the temperature to 0 C.Brine and diethyl ether were added to the mixture, and after sufficient shaking, the organic layer was separated and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was then filtered, and the solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (1.62 g, 162 mmol).1H-NMR (CDCl3) delta: 2.07-2.14 (m, 2H), 2.54 (t, J=6.8 Hz, 2H), 3.82-3.88 (m, 2H), 4.03 (s, 2H).

Reference： [1]Heterocycles,2011,vol. 82,p. 1267 - 1282
[2]Patent: CN107382928,2017,A .Location in patent: Paragraph 0007-0008; 0010-0011; 0013-0014
[3]Liebigs Annalen der Chemie,1983,p. 1950 - 1958
[4]Tetrahedron,2003,vol. 59,p. 1453 - 1467
[5]Patent: CN104650049,2018,B .Location in patent: Paragraph 0603; 0604
[6]Canadian Journal of Chemistry,1983,vol. 61,p. 1924 - 1932
[7]Tetrahedron,2004,vol. 60,p. 10411 - 10418
[8]Patent: WO2009/85256,2009,A1 .Location in patent: Page/Page column 70-71
[9]Patent: US2009/259049,2009,A1 .Location in patent: Page/Page column 10-11
[10]Patent: WO2010/57121,2010,A1 .Location in patent: Page/Page column 156
[11]Patent: US2010/160280,2010,A1 .Location in patent: Page/Page column 133; 134
[12]Patent: US2011/86882,2011,A1 .Location in patent: Page/Page column 21

2
[ 23462-75-1 ]
[ 61424-76-8 ]
[ 38518-76-2 ]

Yield	Reaction Conditions	Operation in experiment
62%	With hydrogenchloride In methanol reflux; 12 h, RT;

Reference： [1]Eiden, Fritz; Wanner, Klaus Th. [Liebigs Annalen der Chemie, 1984, # 11, p. 1759 - 1777]

3
[ 98166-29-1 ]
[ 23462-75-1 ]

Reference： [1]Archiv der Pharmazie,1985,vol. 318,p. 548 - 555

4
[ 23462-75-1 ]
ethyl acetate n-hexane [ No CAS ]
[ 101166-65-8 ]
[ 108-91-8 ]
[ 145386-59-0 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; citric acid; In tetrahydrofuran; hexane; benzene;	Reference Example 22 In benzene (100 ml) was dissolved tetrahydropyran-3-one (35.1 g) followed by addition of cyclohexylamine (40 ml) with ice-cooling the mixture was-stirred at the same temperature for 30 minutes and, then, refluxed for 1 hour, with the byproduct water being distilled off. After cooling to room temperature, the reaction mixture was added dropwise to 1.6M n-butyllithium in hexane (230 ml) in dry THF (350 ml) with ice-cooling over 30 minutes and the mixture was stirred at the same temperature for 30 minutes. Then, a solution of 2-(tert-butyldimethylsilyloxy)ethyl iodide (75 g) in THF (140 ml) was added with ice-cooling over 20 minutes and the mixture was stirred at the same temperature for 1 hour. Then, 10percent aqueous solution of citric acid (1 l) was added and the mixture was vigorously stirred. This reaction mixture was shaken with hexane (3 l) and the organic layer was separated. The organic layer was washed with water and aqueous sodium chloride solution in that order, and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by column chromatography (stationary phase: silica gel 1 kg; ethyl acetate-hexane 1:10) to give 42.8 g of 4-[2-(tert-butyldimethylsilyloxy)ethyl]-3-oxotetrahydropyran as light yellow oil. IR (Neat): 2960, 2930, 2850, 1720 cm -1

Reference： [1]Patent: US5459260,1995,A

5
[ 19752-84-2 ]
[ 23462-75-1 ]
tetrahydro-3-methyl-3-(phenylmethoxy)-2H-pyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With methylmagnesium bromide; ammonium chloride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;	EXAMPLE 2 Tetrahydro-3-methyl-3-(phenylmethoxy)-2H-pyran (2) 53.78 g of pyridinium chlorochromate was stirred in 230 ml of methylene chloride under a nitrogen atmosphere at room temperature, and a solution of 11.97 g of 1A in 20 ml of methylene chloride was added to the stirred mixture. After 17 hours at room temperature, the mixture was diluted with twice its volume of anhydrous ether, and the resulting liquid phase was decanted, passed through a florisil filter and stripped of solvent. The residue was vacuum distilled, the fraction boiling at 70 C., 22 Torr, being dihydro-2H-pyran-3(4H)-one (2A). 13.5 ml of 3 M methyl magnesium bromide in ether was added drop by drop to a stirred solution of 4.00 g of 2A in 22 ml of tetrahydrofuran under a nitrogen atmosphere at -55 C.--47 C. Over a two-hour period, the resulting mixture was allowed to warm to room temperature. 10 ml of saturated ammonium chloride solution was added, and 15 minutes later the organic phase was separated, dried (MgSO4) and stripped of solvent to give residue A. The aqueous phase was partially stripped of water and extracted with methylene chloride; the extract was dried (MgSO4) and stripped of solvent to give residue B. Residues A and B were combined and distilled. The fraction boiling at 55 C., 5.5 Torr., was identified as tetrahydro-3-methyl-2H-pyran-3-ol (2B). 2 was obtained as a pale green liquid, boiling point not determined, by treating 2B with benzyl chloride according to the procedure described for converting 1A to 1.

Reference： [1]Patent: US4388104,1983,A

6
[ 23462-75-1 ]
[ 1378680-33-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide; bromine In chloroform at 50℃;

Reference： [1]Walter; Von Coburg; Isensee; Sander; Ligneau; Camelin; Schwartz; Stark [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 19, p. 5879 - 5882]

7
[ 23462-75-1 ]
[ 107-91-5 ]
[ 848324-33-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfur; diethylamine In ethanol Reflux;

Reference： [1]Location in patent: scheme or table Jamieson, Craig; Basten, Stephanie; Campbell, Robert A.; Cumming, Iain A.; Gillen, Kevin J.; Gillespie, Jonathan; Kazemier, Bert; Kiczun, Michael; Lamont, Yvonne; Lyons, Amanda J.; MacLean, John K.F.; Moir, Elizabeth M.; Morrow, John A.; Papakosta, Marianthi; Rankovic, Zoran; Smith, Lynn [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 19, p. 5753 - 5756]

8
[ 23462-75-1 ]
[ 873397-34-3 ]

Reference： [1]Heterocycles,2011,vol. 82,p. 1267 - 1282

9
[ 23462-75-1 ]
[ 212127-81-6 ]

Reference： [1]Patent: WO2016/89797,2016,A1
[2]Patent: WO2017/176961,2017,A1

10
[ 23462-75-1 ]
[ 73183-34-3 ]
[ 212127-81-6 ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 666 - 670

11
[ 23462-75-1 ]
[ 5331-43-1 ]
C₁₃H₁₈N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		Step 1: The mixture of 38_1 (1.20 g, 11.99 mmol, 1.40 eq) and benzyl N- aminocarbamate (1.42 g, 8.56 mmol, 1.00 eq) in MeOH (15 mL) was stirred at 30C for 2 h. NaBCN (2.69 g, 42.82 mmol, 5.00 eq) was added. The resulting mixture was stirred at 30 C for 16 h. The mixture was concentrated and diluted with water (50 mL) and EA (50 mL). The organic layer was concentrated and purified by column chromatography (PE:EA=10:1~2:1) to give 38_2 (1.50 g, 5.99 mmol, 70% yield) as a colorless oil. LCMS: RT = 0.568 min, m/z 273.2 [M+H]+ NMR (CDCb, 400 MHz) S 7.40-7.35 (m, 5H), 6.25 (s, 1H), 5.26-5.14 (m, 2H), 3.86-3.73 (m, 3H), 3.48-3.30 (m, 2H), 1.91-1.85 (m, 2H), 1.59-1.46(m, 2H).

Reference： [1]Patent: WO2017/21969,2017,A1 .Location in patent: Page/Page column 41

12
[ 23462-75-1 ]
[ 2181-42-2 ]
[ 185-75-1 ]

Yield	Reaction Conditions	Operation in experiment
35%	Stage #1: trimethylsulphonium iodide With sodium hydride In dimethyl sulfoxide; mineral oil at 5℃; for 0.5h; Inert atmosphere; Stage #2: 5,6-dihydro-2H-pyran-3(4H)-one In dimethyl sulfoxide; mineral oil at 15℃; for 20h;	15.1 Step 1. Synthesis of Intermediate 11-2. Step 1. Synthesis of Intermediate 11-2. To a mixture of trimethylsulfoxonium iodide (12.2 g, 59.8 mmol) in DMSO (40 mL) was added NaH (2.38 g, 60% in mineral oil, 59.8 mmol) portionwise at 5 °C under N2 and the mixture was stirred at 5 °C for 30 mins. Intermediate 11- 1 (5 g, 49.9 mmol) in DMSO (40 mL) was added dropwise maintaining the temperature below 15 °C and stirring was continued at 15 °C for 20 hrs. The reaction was quenched at 10 °C with water (200 mL) and extracted with DCM (2 x 200 mL). The combined organic phases were washed with brine (200 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (0%~50% EtOAc in PE) to afford Intermediate 11-2 (2 g, 35%) as a colorless oil. (0356) 1H NMR (400 MHz, CDCl3) δ 3.81-3.60 (m, 3H), 3.49 (d, J = 12.0 Hz, 1H), 2.73-2.65 (m, 2H), 2.03-1.82 (m, 2H), 1.81-1.62 (m, 2H).

Reference： [1]Current Patent Assignee: SAZCHI TREAT STOCK; SAGE THERAPEUTICS INC - WO2017/173358, 2017, A1 Location in patent: Paragraph 00136

13
[ 23462-75-1 ]
[ 1030268-24-6 ]
[ 185-75-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate In 1,2-dimethoxyethane at 80℃; for 16h; Inert atmosphere;	135.1 Step 1: 1,7-dioxaspiro[2.5]octane [00520] To a solution of 142-1 (200.0 mg, 2.0 mmol, 1.0 eq) in DME (4.0 mL) was added t-BuOK (224.4 mg, 2.0 mmol, 1.0 eq) and 142-2 (484.2 mg, 2.2 mmol, 1.1 eq). The mixture was stirred at 80 C for 16 hour under an N2 atmosphere. TLC (Petroleum ether : ethyl acetate=3/l) showed a new spot appeared. The reaction was filtered and concentrated under reduced pressure to give a crude product. The crude product was diluted with water (5 mL) and washed with EtOAc (lOmL x 2). The combined organic layers were concentrated to give crude 142-3 (60. 0 mg, 0.53 mmol, 26.3% yield) as a yellow oil.

Reference： [1]Current Patent Assignee: VIVACE THERAPEUTICS - WO2018/204532, 2018, A1 Location in patent: Paragraph 00520

14
[ 23462-75-1 ]
[ 131747-54-1 ]
3-(3-(hydroxymethyl)pyridin-2-yl)tetrahydro-2H-pyran-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25.8%	Stage #1: 2-bromo-3-hydroxymethylpyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; Stage #2: 5,6-dihydro-2H-pyran-3(4H)-one In tetrahydrofuran; hexane at -78 - 20℃; for 2h;	11.1 Step 1 Synthesis of 3-(3-(hydroxymethyl)pyridin-2-yl)tetrahydro-2H-pyran-3-ol Add (2-bromopyridin-3-yl)methanol (8.00g, 42.54mmol) methanol to a 250 mL round-bottom flask, nitrogen protection, add anhydrous THF (100 mL), cool to -78 °C. Add n-butyl lithium (37.0mL, 93.60mmol, 2.5mol/L) n-hexane solution dropwise, add it for 30min, stir at -78 °C for 1h, add tetrahydropyran-3-one (4.73mL, 51.05mmol), stir insulation for 30min, and then continue stirring at room temperature for 90min. 20mL of saturated ammonium chloride aqueous solution was added to quench, ethyl acetate extract (3×20mL), anhydrous sodium sulfate dried, filtered, concentrated under reduced pressure, the resulting residue was purified by column chromatography (petroleum ether / ethyl acetate (v / v) = 1:3), to give the title compound is a viscous colorless oily liquid 2.30g, yield 25.8%.
25.8%	Stage #1: 2-bromo-3-hydroxymethylpyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; Stage #2: 5,6-dihydro-2H-pyran-3(4H)-one In tetrahydrofuran; hexane at -78 - 20℃; for 2h;	11.1 Step 1 Synthesis of 3-(3-(hydroxymethyl)pyridin-2-yl)tetrahydro-2H-pyran-3-ol Add (2-bromopyridin-3-yl)methanol (8.00g, 42.54mmol) methanol to a 250 mL round-bottom flask, nitrogen protection, add anhydrous THF (100 mL), cool to -78 °C. Add n-butyl lithium (37.0mL, 93.60mmol, 2.5mol/L) n-hexane solution dropwise, add it for 30min, stir at -78 °C for 1h, add tetrahydropyran-3-one (4.73mL, 51.05mmol), stir insulation for 30min, and then continue stirring at room temperature for 90min. 20mL of saturated ammonium chloride aqueous solution was added to quench, ethyl acetate extract (3×20mL), anhydrous sodium sulfate dried, filtered, concentrated under reduced pressure, the resulting residue was purified by column chromatography (petroleum ether / ethyl acetate (v / v) = 1:3), to give the title compound is a viscous colorless oily liquid 2.30g, yield 25.8%.

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2022/33544, 2022, A1 Location in patent: Page/Page column 54-55
[2]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2022/33544, 2022, A1 Location in patent: Page/Page column 54-55

15
[ 23462-75-1 ]
[ 5428-40-0 ]
N-(4-methyl-3-(4-oxo-3,4,5',6'-tetrahydro-2'H,4'H-spiro[benzo[e][1,3]oxazine-2 ,4'-pyran]-7-yl)phenyl)-2-(trifluoromethyl)isonicotinamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2022,vol. 63

16
[ 23462-75-1 ]
[ 5428-40-0 ]
C₁₂H₁₂BrNO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium(II) sulfate; toluene-4-sulfonic acid; In 1,4-dioxane; toluene; at 110℃;Inert atmosphere;	General procedure: To a solution of <strong>[5428-40-0]4-bromo-2-hydroxybenzamide</strong> 9a (2.8 g, 13 mmol), tetrahydro-4H-pyran-4-one(2.6 mL, 26 mmol) and p-toluenesulfonic acid monohydrate (494 mg, 2.6 mmol) in 1,4-dioxaneand toluene (60 + 100 mL), magnesium sulfate (4.68 g, 38.87 mmol) was added. The mixture wasrefluxed overnight at which point LC-MS showed 80% conversion. More tetrahydro-4H-pyran-4-one (1.2 mL, 12 mmol), p-toluenesulfonic acid monohydrate (120 mg, 0.24 mmol) were added andthe mixture was refluxed for 6 h. The solid was filtered off and the filtrate was concentrated underreduced pressure. EtOAc (300 mL) was added, and the organic phase was washed by saturatedNaHCO3 and brine. The organic phase was dried over MgSO4. The MgSO4 solid was removed,and the filtrate was concentrated to result compound 9b (3.26 g, yield 84%) as pale solid.
	With magnesium(II) sulfate; toluene-4-sulfonic acid; In 1,4-dioxane; toluene; at 110℃;Inert atmosphere;	General procedure: To a solution of <strong>[5428-40-0]4-bromo-2-hydroxybenzamide</strong> 9a (2.8 g, 13 mmol), tetrahydro-4H-pyran-4-one(2.6 mL, 26 mmol) and p-toluenesulfonic acid monohydrate (494 mg, 2.6 mmol) in 1,4-dioxaneand toluene (60 + 100 mL), magnesium sulfate (4.68 g, 38.87 mmol) was added. The mixture wasrefluxed overnight at which point LC-MS showed 80% conversion. More tetrahydro-4H-pyran-4-one (1.2 mL, 12 mmol), p-toluenesulfonic acid monohydrate (120 mg, 0.24 mmol) were added andthe mixture was refluxed for 6 h. The solid was filtered off and the filtrate was concentrated underreduced pressure. EtOAc (300 mL) was added, and the organic phase was washed by saturatedNaHCO3 and brine. The organic phase was dried over MgSO4. The MgSO4 solid was removed,and the filtrate was concentrated to result compound 9b (3.26 g, yield 84%) as pale solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2022,vol. 63
[2]Bioorganic and Medicinal Chemistry Letters,2022,vol. 63

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[ CAS No. 23462-75-1 ] {[proInfo.proName]}

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[ 23462-75-1 ] Synthesis Path-Upstream 1~15

[ 23462-75-1 ] Synthesis Path-Downstream 1~16

Related Functional Groups of [ 23462-75-1 ]

Ketones

Related Parent Nucleus of [ 23462-75-1 ]

Aliphatic Heterocycles

Tetrahydropyrans

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[ 23462-75-1 ]

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[ 23462-75-1 ]