[ CAS No. 77342-93-9 ]

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2D3D

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Quality Control of [ 77342-93-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 77342-93-9 ]

SDS

Alternatived Products of [ 77342-93-9 ]

Product Details of [ 77342-93-9 ]

CAS No. :	77342-93-9	MDL No. :	MFCD03789633
Formula :	C₆H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	114.14	Pubchem ID :	10129928
Synonyms :

Computed Properties of [ 77342-93-9 ]

TPSA :Topological Polar Surface Area	26.3	H-Bond Acceptor Count :	2
XLogP3 :	0	H-Bond Donor Count :	0
SP3 :	0.83	Rotatable Bond Count :	1

Safety of [ 77342-93-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 77342-93-9 ]

Upstream synthesis route of [ 77342-93-9 ]
Downstream synthetic route of [ 77342-93-9 ]

[ 77342-93-9 ] Synthesis Path-Upstream 1~2

1
[ 13417-49-7 ]
[ 77342-93-9 ]

Yield	Reaction Conditions	Operation in experiment
91.6%	With palladium 10% on activated carbon; hydrogen In methanol	10percent Pd/C (600 mg) was slowly added to a solution of Compound-2 (6 g, 53.5 mmol) in methanol (10 mL) and the mixture was stirred under hydrogen(40 psi). The reaction mixture was filtered through celite, the precipitate was rinsed with methanol and the filtrate was concentrated under vacuum. The residue was purified by fractional distillation at 125 °C/20 mm Hg to obtain Compound-3 (5.5 g, 91.6percent). MS (m/z): [M + H]+,115.1.
91.6%	With palladium 10% on activated carbon; hydrogen In methanol	10percent Pd/C (600 mg) was slowly added to a solution of Compound-2 (6 g, 53.5 mmol) in methanol (10 mL) and the mixture was stirred under hydrogen (40 psi). The reaction mixture was filtered through celite, the precipitate was rinsed with methanol and the filtrate was concentrated under vacuum. The residue was purified by fractional distillation at 125 °C/20 mm Hg to obtain Compound-3 (5.5 g, 9 1.6percent). MS (m/z): [M + H1, 115.1.

Reference： [1] Molecular Pharmacology, 2015, vol. 87, # 3, p. 477 - 491
[2] Patent: WO2016/85939, 2016, A2, . Location in patent: Paragraph 00260
[3] Patent: US5071863, 1991, A,
[4] Chemistry and Industry (London, United Kingdom), 1955, p. 1772
[5] Chemistry and Industry (London, United Kingdom), 1955, p. 1772
[6] Patent: US2514156, 1946, ,
[7] Patent: US2514156, 1946, ,
[8] Patent: WO2008/101867, 2008, A1, . Location in patent: Page/Page column 67

2
[ 110-87-2 ]
[ 50-00-0 ]
[ 142-68-7 ]
[ 100-72-1 ]
[ 14774-36-8 ]
[ 19611-45-1 ]
[ 77342-93-9 ]

Reference： [1] Transition Metal Chemistry, 2013, vol. 38, # 7, p. 787 - 792

[ 77342-93-9 ] Synthesis Path-Downstream 1~7

1
[ 13417-49-7 ]
[ 77342-93-9 ]

Yield	Reaction Conditions	Operation in experiment
91.6%	With palladium 10% on activated carbon; hydrogen; In methanol; under 2068.65 Torr;	10% Pd/C (600 mg) was slowly added to a solution of Compound-2 (6 g, 53.5 mmol) in methanol (10 mL) and the mixture was stirred under hydrogen(40 psi). The reaction mixture was filtered through celite, the precipitate was rinsed with methanol and the filtrate was concentrated under vacuum. The residue was purified by fractional distillation at 125 C/20 mm Hg to obtain Compound-3 (5.5 g, 91.6%). MS (m/z): [M + H]+,115.1.
91.6%	With palladium 10% on activated carbon; hydrogen; In methanol;	10% Pd/C (600 mg) was slowly added to a solution of Compound-2 (6 g, 53.5 mmol) in methanol (10 mL) and the mixture was stirred under hydrogen (40 psi). The reaction mixture was filtered through celite, the precipitate was rinsed with methanol and the filtrate was concentrated under vacuum. The residue was purified by fractional distillation at 125 C/20 mm Hg to obtain Compound-3 (5.5 g, 9 1.6%). MS (m/z): [M + H1, 115.1.
85%	palladium-carbon; In methanol;	1. 3-Formyl-tetrahydro-2H-pyran 5% Pd/C (5 g) was added to a solution of <strong>[13417-49-7]3-formyl-5,6-dihydro-2H-pyran</strong>1) (95.8 g, 0.81 mol) in MeOH (200 ml) at room temperature, and the mixture was stirred for 15 hours under a hydrogen atmosphere. The catalyst was filtered off, and the solvent was removed in vacuo. The resulting oil was distilled under reduced pressure (84-85 C./36-39 mmHg) to give 3-formyl-tetrahydro-2H-pyran (79.4 g, 85% yield). 1) Japan Kokaitokkyo Koho 84167584 (1984) 1H NMR: (CDCl3), 1.59-1.72 (m, 2H), 1.82-1.98 (m, 2H), 2.44-2.54 (m, 1H), 3.52-3.61 (m, 1H), 3.68-3.74 (m, 1H), 3.82 (dd, 1H, J=11.7, 6.6 Hz), 3.97 (dd, 1H, J=11.7, 3.7 Hz), 9.72 (s, 1H).

With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 0.5h;

Intermediate 25: Tetrahvdro-2H-pyran-3-carbaldehvde5,6-Dihydro-2H-pyran-3-carbaldehyde (2.98 gm) in ethanol (70 ml) was treated with 10% wetted palladium on carbon catalyst under nitrogen, then hydrogenated at ambient temperature and pressure for 30 min. The catalyst was filtered off through Celite and the filtrate evaporated, then re-evaporated from toluene to give the product as an oil, yield 2.58g.1H NMR (CDCI3): delta 9.72 (1 H, s), 3.98 (1 H, m), 3.82 (1 H, m), 3.73 (1 H, m), 3.58 (1 H, m), 2.49 (1 H, m), 1.95 (1 H, m), 1.87 (1 H, m), 1.70 (1 H, m), 1.61 (1 H, m).

Reference： [1]Molecular Pharmacology,2015,vol. 87,p. 477 - 491
[2]Patent: WO2016/85939,2016,A2 .Location in patent: Paragraph 00260
[3]Patent: US5071863,1991,A
[4]Chemistry and industry,1955,p. 1772
[5]Chemistry and industry,1955,p. 1772
[6]Patent: US2514156,1946,
[7]Patent: US2514156,1946,
[8]Patent: WO2008/101867,2008,A1 .Location in patent: Page/Page column 67

2
[ 77342-93-9 ]
[ 4312-99-6 ]
[ 77342-70-2 ]

Yield	Reaction Conditions	Operation in experiment
68%	With triethylamine In ethanol at 80℃; for 15h;

Reference： [1]Stetter, Hermann; Mohrmann, Karl-Heinrich; Schlenker, Walter [Chemische Berichte, 1981, vol. 114, # 2, p. 581 - 596]

3
[ 77342-93-9 ]
[ 14774-36-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium tetrahydroborate; In methanol; dichloromethane; at -10 - 20℃; for 4.0h;	[00174] At -5 C-10 C, to a solution of tetrahydro-2H-pyran-3-carbaldehyde (450 mg, 3.943 mmol) in the co-solvent of DCM/MeOH(6 mL, 15:1 ) was added NaBH4 (90 mg, 2.366 mmol) in several portions. The mixture was stirred at rt for 4 h. Then at 0 C, to the mixture was added 1 N HCI aq. until no bubble appeared. The mixture was extracted with DCM for 3 times. The organic layer was combined, dried over anhydrous Na2S04, filtered and concentrated to give the title ccompound (416 mg, 91 %) as colorless oil. 1H NMR (300 MHz, DMSO-c/6) delta ppm 4.05 - 3.57 (m, 2H), 3.45 - 3.22 (m, 4H), 3.17 (t, 1 H), 1 .89 - 1 .43 (m, 4H), 1 .37 - 1 .08 (m, 1 H). LC-MS: [M+H]+ = 117.0.
	With hydrogenchloride; sodium borohydrid; In methanol; dichloromethane; water;	3.3 3-Hydroxymethyltetrahydropyran 5 g of 3-formyltetrahydropyran (prepared according to the process described in U.S. Pat. No. 5,149,821) are dissolved in a 60/4 mixture of dichloromethane and methanol, followed by cooling to a temperature between 0 and -5 C. and addition of 0.831 g of sodium borohydride in 8 portions. When the addition is complete, the mixture is allowed to warm to 10 C. and is left at this temperature for 40 min. The mixture is then cooled to 0 C. and a mixture of 20 ml of water and 2 ml of hydrochloric acid is then added dropwise. The temperature rises to 10 C. The phases are separated after settling has taken place and the aqueous phase is extracted with 6 times 25 ml of dichloromethane, dried over sodium sulphate and filtered, and the solvent is evaporated off. 4.13 g of product are obtained. The aqueous phase, saturated with sodium chloride, is re-extracted with 3 times 30 ml of dichloromethane. A further 0.270 g of product is obtained, giving 4.4 g of product in total.

Reference： [1]Patent: WO2017/149463,2017,A1 .Location in patent: Paragraph 00174
[2]Patent: US5525619,1996,A

4
[ 110-87-2 ]
[ 50-00-0 ]
[ 142-68-7 ]
[ 100-72-1 ]
[ 14774-36-8 ]
[ 19611-45-1 ]
[ 77342-93-9 ]
bis(2-tetrahydropyranyl)methanol [ No CAS ]
2-tetrahydropyranyl tetrahydropyran-2-carboxylate [ No CAS ]

Reference： [1]Transition Metal Chemistry,2013,vol. 38,p. 787 - 792

5
[ 77342-93-9 ]
[ 930785-40-3 ]
tert-butyl 4-(tetrahydro-2H-pyran-3-ylmethyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%		Titanium(IV) isopropoxide (998 mg, 3.51 mmol) was added to a mixture of C23 (300 mg, 1.17 mmol) and tetrahydro-2 --pyran-3-carbaldehyde (160 mg, 1.40 mmol) in ethanol (10 mL) at 27 C, and the reaction mixture was stirred at 27 C for 15 hours. It was then cooled to 0 C, treated with sodium borohydride (88.6 mg, 2.34 mmol), and allowed to stir at 25 C for 4 hours. Water (10 mL) was added slowly, and the resulting mixture was stirred at 25 C for 30 minutes. After combination with a mixture derived from a smaller-scale reaction carried out on C23 (50 mg, 0.20 mmol), this was extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried, filtered, and concentrated in vacuo; purification via chromatography on silica gel (Gradient: 0% to 5% methanol in dichloromethane) provided the product as a colorless oil. Starting material C23 (200 mg) was also recovered, as a yellow gum. Yield: 106 mg, 0.299 mmol, 22% (51 % based on recovered starting material). LCMS m/z 355.3 [M+H]+. 1H NMR (400 MHz, CDCI3) delta 3.96-3.88 (m, 1 H), 3.88-3.80 (m, 1 H), 3.79-3.58 (m, 4H), 3.42-3.33 (m, 1 H), 3.19-3.04 (m, 3H), 2.42-2.33 (m, 1 H), 2.33-2.26 (m, 1 H), 2.26-2.19 (m, 1 H), 2.15-2.01 (m, 3H), 1.98-1.73 (m, 5H), 1.64-1.53 (m, 2H), 1.44 (s, 9H), 1.44-1.34 (m, 2H).
		This synthesis was carried out in library format. Amixture oftetrahydro-2H-pyran-3-carbaldehyde (163 f.tmol,1.3 equivalents) and PI [0.125 M solution in (0.0125 Msolution of acetic acid in 1,2-dichloroethane); 1.0 mL, 125f.tmol, 1.0 equivalent] was shaken at 30 C. for 16 hours ina closed vial, whereupon sodium triacetoxyborohydride(250 flillOl, 2.0 equivalents) was added, and shaking wascontinued at 30 C. for an additional 16 hours. Solvent wasremoved using a SpeedVac evaporator, and the residue waspurified via preparative thin-layer chromatography on silicagel to provide Cl7 (tert-butyl 4-(tetrahydro-28-pyran-3-ylmethyl)-1-oxa-4,9-diazaspiro[ 5 .S]undecane-9-carboxylate).This material was dissolved in methanol (500 f.LL),treated with hydrogen chloride in methanol ( 4.0 M; 1.0 mL,4.0 mmol), and shaken at 30 C. for 2 hours. Concentrationusing a SpeedVac evaporator provided intermediate CIS( 4-(tetrahydro-2H -pyran-3-ylmethyl)-1-oxa-4,9-diazaspiro[5.5]undecane, hydrochloride salt).

Reference： [1]Patent: WO2017/21805,2017,A1 .Location in patent: Page/Page column 83; 85
[2]Patent: US2018/208608,2018,A1 .Location in patent: Paragraph 0293; 0294

6
[ 77342-93-9 ]
[ 116131-44-3 ]

Reference： [1]Patent: WO2017/149463,2017,A1

7
[ 873397-34-3 ]
[ 77342-93-9 ]

Reference： [1]Patent: EP3418282,2018,A1

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[ CAS No. 77342-93-9 ]

Quality Control of [ 77342-93-9 ]

Related Doc. of [ 77342-93-9 ]

Product Details of [ 77342-93-9 ]

Computed Properties of [ 77342-93-9 ]

Safety of [ 77342-93-9 ]

Application In Synthesis of [ 77342-93-9 ]

[ 77342-93-9 ] Synthesis Path-Upstream 1~2

[ 77342-93-9 ] Synthesis Path-Downstream 1~7

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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