[ CAS No. 4255-62-3 ]

Name: 4255-62-3|4,4-Dimethylcyclohexanone|98%
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CAS No. :	4255-62-3	MDL No. :	MFCD00234965
Formula :	C₈H₁₄O	Boiling Point :	170.6°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	126.20 g/mol	Pubchem ID :	138166
Synonyms :

Safety of [ 4255-62-3 ]

Signal Word:	Danger	Class:	4.1
Precautionary Statements:	P264-P210-P240-P280-P305+P351+P338-P337+P313-P370+P378-P403+P233-P501	UN#:	1325
Hazard Statements:	H228-H319	Packing Group:	Ⅱ
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Application In Synthesis of [ 4255-62-3 ]

Upstream synthesis route of [ 4255-62-3 ]
Downstream synthetic route of [ 4255-62-3 ]

[ 4255-62-3 ] Synthesis Path-Upstream 1~6

1
[ 4255-62-3 ]
[ 932-01-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2365 - 2369
[2] Bulletin des Societes Chimiques Belges, 1980, vol. 89, # 5, p. 389 - 398
[3] Journal of the American Chemical Society, 1968, vol. 90, # 23, p. 6486 - 6492
[4] Journal of the American Chemical Society, [5] Journal of the American Chemical Society, 2009, vol. 131, p. 251 - 262
[6] Organic and Biomolecular Chemistry, 2012, vol. 10, # 36, p. 7321 - 7326

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[ 1073-13-8 ]
[ 932-01-4 ]
[ 5020-09-7 ]
[ 4255-62-3 ]

Reference： [1] Tetrahedron, 1980, vol. 36, p. 1937 - 1942
[2] European Journal of Organic Chemistry, 2000, # 9, p. 1793 - 1797

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[ 2979-19-3 ]
[ 1193-46-0 ]
[ 932-01-4 ]
[ 767-12-4 ]
[ 1193-47-1 ]
[ 4255-62-3 ]

Reference： [1] Journal of the American Chemical Society, 2015, vol. 137, # 50, p. 15833 - 15842

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[ 4255-62-3 ]
[ 20615-18-3 ]

Yield	Reaction Conditions	Operation in experiment
83 %Chromat.	at 20℃; for 2.5 h; Sonication; Green chemistry	General procedure: Ni-Al alloy (200 mg) and cyclohexanone (35 μL, 0.34 mmol) were suspended in 28–30percent NH₄OH (3 mL) and sonicated (Branson 1510MTH ultrasonic bath) for 2 h. After the completion of the reaction, the excess alloy and solid by-products were removed by filtration. The filtrate was extracted with EtOAc (2 × 2 mL). The organic extracts were combined and dried over anhyd Na₂SO₄. The solvent was removed in vacuo and the crude product was purified by flash chromatography.

Reference： [1] Patent: WO2014/37900, 2014, A1,
[2] Synthesis (Germany), 2016, vol. 48, # 18, p. 3127 - 3133

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[ 4255-62-3 ]
[ 616-38-6 ]
[ 50388-51-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.5 h; Stage #2: at 0 - 80℃; for 3.5 h;	Example 8 l-(2-(bromomethyl)-4,4-dimethylcyclohex-l-enyl)-4-chlorobeπzene <n="44"/>ξ fTo a solution of 21 g of dimethyl carbonate (0.23 mol) in dry THF (400 ml) was added sodium hydride (9.6 g, 0.24 mol) by portion at 0 ⁰C. The resulting mixture was stirred at 0 ⁰C for 30 min and then was added a solution of 10 g of compound a (79 mmol) in THF (100 ml) dropwise over 30min. The resultant mixture was heated to 60⁰C - 80⁰C for 3h before cooled to room temperature. The reaction mixture was poured into saturated NaHCO₃ solution and extracted with ether. The organic layer was washed with water, brine, dried over Na₂SO₄ and concentrated to give 25 g of of intermediate b methyl 5,5-dimethyl-2-oxocyclohexanecarboxylate (yield: 84percent). MS (ESI) m/e (M+H⁺): 185.
84%	Stage #1: With sodium hydride In tetrahydrofuran at 0℃; Stage #2: at 60 - 80℃; Stage #3: With water; sodium hydrogencarbonate In tetrahydrofuran	Example 3Preparation of 1 N- { 1- [ 4- (4 ' -Chloro-biphenyl-2-ylmethyl) - piperazin-1-yl] -quinazolin-4-yl}-4- ( (R) -3-dimethylamino-l- phenylsulfanylmethyl-propylamino) -3-nitro-benzenesulfonamide To a solution of 21 g of dimethyl carbonate (0.23 mol) in dry THF (400 ml) was added sodium hydride (9.6 g, 0.24 mol) by portion at 0 ⁰C. The resulting mixture was stirred at 0 ⁰C for 30 min and then was added a solution of 10 g of compound a (79 mmol) in THF (100 ml) dropwise over 30min. The resultant mixture was heated to 60 ⁰C - 80 ⁰C for 3h before cooled to room temperature. The reaction mixture was poured into saturated NaHCψ3 solution and extracted with ether. The organic layer was washed with water, brine, dried over Na₂SO₄ and concentrated to give 25 g of of intermediate b methyl 5, 5-dimethyl-2- oxocyclohexanecarboxylate (yield: 84percent) . MS (ESI) m/e (M+H⁺) : 185.

Reference： [1] Journal of Organic Chemistry, 1998, vol. 63, # 8, p. 2548 - 2559
[2] Canadian Journal of Chemistry, 1988, vol. 66, p. 2345 - 2347
[3] Canadian Journal of Chemistry, 1997, vol. 75, # 6, p. 742 - 753
[4] Patent: WO2008/61208, 2008, A2, . Location in patent: Page/Page column 42-43
[5] Patent: WO2009/143246, 2009, A2, . Location in patent: Page/Page column 210
[6] Journal of Medicinal Chemistry, 2016, vol. 59, # 20, p. 9431 - 9442
[7] Journal of Organic Chemistry, 1981, vol. 46, # 26, p. 5434 - 5436
[8] Angewandte Chemie - International Edition, 2003, vol. 42, # 24, p. 2785 - 2788
[9] Patent: US2010/184766, 2010, A1, . Location in patent: Page/Page column 46

6
[ 4255-62-3 ]
[ 1044598-91-5 ]

Reference： [1] Patent: WO2017/101851, 2017, A1,
[2] Patent: WO2017/123616, 2017, A1,

[ 4255-62-3 ] Synthesis Path-Downstream 1~25

1
[ 932-01-4 ]
[ 4255-62-3 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1913,vol. 401,p. 313
Justus Liebigs Annalen der Chemie,1915,vol. 409,p. 164

2
[ 1073-13-8 ]
[ 4255-62-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogen;palladium on activated charcoal; In pentane; under 1292.9 Torr; for 0.5h;	Preparation Example A2- 1 : 4,4-dimethyl-cyclohexanone; [482] 4,4-Dimethyl-cyclohexene-l-one (5 g, 40.3 mmol) and n-pentane (15 ml) were placed in a hydrogen reaction vessel, and Pd/C (500 mg) was added. The hydrogen reaction vessel was pressurized with hydrogen (25 psi), and reacted for 30 min. After the reaction finished, the reaction mixture was filtered through Celite, and the filtrate was concentrated in vacuo to give the title compound (5 g, 98 %).[483] MS[M+H] = 127(M+1)
98%	With hydrogen;1% Pd/C; In pentane; for 0.5h;	Preparation 4 4,4-dimethyl-cyclohexanone 4,4-dimethyl-cyclohexen-1-one (5 g, 40.3 mmol) were placed in a hydrogen reaction vessel and n-pentane (15 ml) was added, and Pd/C (500 mg) was added thereto. The hydrogen reaction vessel was pressurized with hydrogen (25 psi), and the reaction was conducted for 30 minutes. After completing the reaction, the solid like material was filtered through Celite and the filtrate was concentrated in vacuo to give the title compound (5 g, 98%). MS[M+H]=127 (M+1)
98%	With hydrogen;1% Pd/C; In pentane; under 1292.9 Torr; for 0.5h;	Preparation 4: 4,4-dimethyl-cyclohexanone[316] 4,4-dimethyl-cyclohexen-l-one (5 g, 40.3 mmol) were placed in a hydrogen reaction vessel and n-pentane (15 ml) was added, and Pd/C (500 mg) was added thereto. The hydrogen reaction vessel was pressurized with hydrogen (25 psi), and the reaction was conducted for 30 minutes. After completing the reaction, the solid like material was filtered through Celite and the filtrate was concentrated in vacuo to give the title compound (5 g, 98 %).[317] MS[M+H] = 127 (M+ 1)

98%	With hydrogen;palladium on activated charcoal; In tetrahydrofuran; at 20℃; for 15h;	A mixture of commercially available 4,4-dimethylcyclohex-2-enone (46 g, 370.97 mmol, 1.00 equiv) and Pd/C (4.6 g) in tetrahydrofuran (250 mL) was stirred for 15 hours at room temperature under a hydrogen atmosphere. The solid was filtered out. The filtrate was concentrated under vacuum. This resulted in 4,4-dimethylcyclohexanone (46 g, 98%) as a solid.
97%	With hydrogen; In ethyl acetate; under 517.162 Torr; for 0.75h;	Preparation 43 4,4-Dimethylcyclohexanone 4,4-Dimethylcyclohexanone was prepared by a procedure similar to that described in patent ref: PCT Int. Appl. 2005005456 20, January 2005. 4,4-Dimethylcyclohex-2-enone (3.5 g, 28.18 mmol) was dissolved in ethyl acetate (50 mL). The solution was shaken for 45 minutes under an atmosphere of hydrogen (10 p.s.i.). The completion of the reaction was established by GC-MS then the solution was filtered through a pad of celite and rinsed through with ethyl acetate. The solvent was removed under reduced pressure to give a clear colorless oil which crystallized on standing (3.45 gm, 97%). 1H NMR (400 MHz, CDCl3) delta 2.29 (m, 4H) 1.61 (m, 4H) 1.04 (s, 6H). MS calc 126.5, found 127.1 (M+H).
94%	With hydrogen;palladium on activated charcoal; In ethyl acetate; at 20℃; under 760.051 Torr;	Eine Loesung von 4, 4-Dimethyl-cyclohex-2-enon (3 mmol) in Ethylacetat wird ueber Nacht bei Raumtemperatur an Pd/C (0. 05 mmol) mit Wasserstoff unter Normaldruck hydriert. Filtrieren ueber Celite und nachfolgendes Eindampfen ergibt 4, 4-Dimethyl-cyclohexanon (355 mg) in 94% Ausbeute (J. Org. Chem. 2001, 66 (3), 733-738).
92%	With hydrogen;palladium 10% on activated carbon; In Petroleum ether; under 760.051 Torr; for 20h;	To 0.1 g of palladium on activated carbon (10%) was added a solution of 4,4-dimethylcyclohex-2-enone (6.23 g, 50 mmol) in petroleum ether. This mixture was stirred under 1 atmosphere of hydrogen for 20 hours. After filtration through celite, the solvent was removed under reduced pressure to afford a white solid (5.7 g, 92%). C8H14O (126.10), LCMS (ESI): 127.11(M++H). 1H NMR (CDCl3, 300 MHz), delta 2.35 (t, 4H), 1.68 (t, 4H), 1.16 (s, 6H).
87%	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 3102.97 Torr; for 4h;	A solution of 4,4-dimethyl-2-cyclohexen-1-one (25.37 g, 0.204 mol) in ethanol at room temperature (200 ML) was treated with 10% Pd/C catalyst (1.5 g) and agitated under 60 psi H2 for 4 hours.The reaction was filtered and the filter cake was washed with ethanol.The filtrate was concentrated to provide the desired product (22.4 g, 87%). MS (CI) m/e 127 (M+H)+.
82%	With hydrogen;palladium on activated carbon; In ethyl acetate; at 20℃;	This compound was prepared according to the method described by H-J Liu, et AL., (Can. J. Chem. (1988), 66,2345) with modification. To a three-neck round-bottomed flask was added palladium on carbon (Degussa Type, 10% wt. (dry basis) ) (0.167 g). The flask was evacuated and then filled with nitrogen and the evacuation/fill cycle was repeated twice more. To the flask was added a solution of 4, 4-dimethyl-2- cyclohexene-1-one (2.1 mL, 2.0 g, 16 mmol) in EtOAc (100 mL). The flask was evacuated and then filled with nitrogen and the EVACUATION/FILL cycle was repeated once more. The flask was evacuated and then filled with hydrogen using a balloon. The reaction mixture was stirred under a hydrogen atmosphere at room temperature overnight. The flask was evacuated and filled with nitrogen. The reaction mixture was filtered through a pad of Celite and the pad was washed with EtOAc. The filtrate was concentrated to give 1.63 g (82%) of compound 20 as a colorless liquid that solidified to a white solid.'HNMR is consistent with that reported in the cited reference. 'H NMR (400 MHz, CDCI3) : 8 1.08 (s, 6 H), 1.65 (t, J = 6.9 Hz, 4 H), 2.33 (t, J = 6. 9 HZ, 4 H).
75%	With hydrogen;palladium 10% on activated carbon; In pentane; under 760.051 Torr; for 14h;	4,4-Dimethylcyclohexenone (2.01 g, 16.2 mmol) was dissolved in pentane (50 mL) and hydrogenated 14 h at 1 atmosphere with 10% palladium on carbon catalyst (0.05 g). The reaction mixture was filtered through Celite and concentrated under reduced pressure to yield 1.54 g of 4,4- dimethylcyclohexanone (75% yield).
67%	With hydrogen;palladium 10% on activated carbon; In ethyl acetate; at 20℃; under 1292.9 Torr; for 3h;	EXAMPLE XIII 4.4-dimethylcyclohexanone 0.5 g 10% palladium on charcoal are added to a solution of 5.00 g 4,4-dimethyl-cyclohex-2-enone in 25 ml of ethyl acetate. The mixture is shaken under a hydrogen pressure of 25 psi for 3 h at ambient temperature. Then the catalyst is filtered off and the solvent is removed. Yield: 3.38 g (67% of theory) Mass spectrum (ESI+): m/z=144 [M+NH4]+
	palladium-carbon; In pentane;	A mixture of 4,4-dimethyl-2-cyclohexenone 25 (5.00 g, 40.26 mmol) and 10% Pd/C (0.10 g) in pentane (70 mL) was hydrogenated at 5 C. at 1 atmosphere of H2. The reaction was allowed to warm to 25 C. for 18 h. The mixture was filtered through Celite, concentrated to 15 mL and cooled in an i-PrOH-dry ice bath. Filtration afforded 4,4-dimethylcyclohexanone 26 (2.60 g, 51%) as a white fluffy solid. 1H NMR (300 MHz, CDCl3) delta 2.35 t, J=7.0, 4H), 1.67 (t, J=7.0, 4H), 1.10 (s, 6H); C NMR (75 MHz, CDCl3) delta 212.6, 39.2, 38.0, 29.9, 27.5; MS (APCI) m/z (%) 159 (M+MeOH+, 20), 127 (M+H+, 100).
	With hydrogen;palladium 10% on activated carbon; In ethyl acetate; at 20℃; under 750.075 Torr; for 2h;	Scaffold A; a); To a solution of 4,4-dimethyl-cyclohex-2-enone (50 g, 403 mmol) in EA (230 mL) a suspension of Pd/C (2.5 g, 10% Pd) in EA is added. The suspension is stirred at rt for 2 h under 1 bar H2. The catalyst is filtered off and the solvent of the filtrate is carefully evaporated to give 4,4-dimethyl-cyclohexanone (50 g) as a colourless oil <n="27"/>which slowly crystallizes; 1H NMR (CDCI3): delta 2.34 (t, J = 6.4 Hz, 4H), 1 .66 (t, J = 6.4 Hz, 4H), 1.09 (s, 6H).
	With hydrogen;palladium 10% on activated carbon; In ethyl acetate; at 20℃; under 750.075 Torr; for 2h;	a) To a solution of 4,4-dimethyl-cyclohex-2-enone (50 g, 403 mmol) in EA (230 mL) a suspension of Pd/C (2.5 g, 10% Pd) in EA is added. The suspension is stirred at rt for 2 h under 1 bar H2. The catalyst is filtered off and the solvent of the filtrate is carefully evaporated to give 4,4-dimethyl-cyclohexanone (50 g) as a colourless oil which slowly crystallizes; 1H NMR (CDCl3): delta 2.34 (t, J=6.4 Hz, 4H), 1.66 (t, J=6.4 Hz, 4H), 1.09 (s, 6H).
	With hydrogen;palladium 10% on activated carbon; In ethyl acetate; at 20℃; under 750.075 Torr; for 2h;	a) To a solution of 4,4-dimethyl-cyclohex-2-enone (50 g, 403 mmol) in EA (230 mL), a suspension of Pd/C (2.5 g, 10% Pd) in EA is added. The suspension is stirred at rt for 2 h under 1 bar H2. The catalyst is filtered off and the solvent of the filtrate is carefully evaporated to give 4,4-dimethyl-cyclohexanone (50 g) as a colourless oil which slowly crystallizes; 1H NMR (CDCl3): delta 2.34 (t, J=6.4 Hz, 4H), 1.66 (t, J=6.4 Hz, 4H), 1.09 (s, 6H).
	With hydrogen;palladium 10% on activated carbon; In ethyl acetate; at 20℃; under 775.743 Torr; for 3h;	Step 1: 4,4-Dimethylcyclohexanone 4,4-Dimethyl-2-cyclohexene-1-one[Aldrich] (5.5 g) was dissolved in 50 ml of ethyl acetate. The solution, along with 0.25 g of 10% Palladium on Carbon (Degussa type E101), was hydrogenated under 15 psi for 3 h at room temperature. The mixture was passed through a Celite pad to remove the catalyst and then was concentrated to dryness in vacuum. The desired 4,4-dimethylcyclohexanone was obtained as a colorless solid (5.56 g). 1H NMR (400 MHz, CDCl3) delta ppm 1.07 (s, 6H), 1.65 (t, J=7 Hz, 4H), 2.35 (t, J=7 Hz, 4H).
	With hydrogen;5%-palladium/activated carbon; In ethyl acetate; under 760.051 Torr; for 14h;	Ma Step A: Preparation of 4,4-dimethylcyclohexanone CI-Ia); A mixture of 4,4-dimethyl-2-cyclohexen-l-one (4.90 g, 39.5 mmol) and palladium (1.68 g of 5 wt. % on activated carbon) in EtOAc (100 mL) was hydrogenated at atmospheric pressure for 14 h. The resulting mixture was filtered through a short column of Celite, eluting copiously with EtOAc. The filtrate was concentrated in vacuo to afford the title compound i- la-
	palladium-carbon; In ethyl acetate;	Step 1: 4,4-Dimethylcyclohexanone A mixture of 4,4-dimethyl-2-cyclohexene-1-one (5.5 g) and 10% Pd/C (0.25 g, wet, Degussa type E101) in EtOAc (50 mL) was hydrogenated under 15 psi for 3 h at room temperature. The mixture was filtered through Celite and the filtrate was concentrated in vacuo affording the title compound as a colorless solid. 1H NMR (400 MHz, CDCl3) delta ppm 1.07 (s, 6H), 1.65 (t, J=7 Hz, 4H), 2.35 (t, J=7 Hz, 4H).
	With hydrogen;palladium 10% on activated carbon; In ethyl acetate; at 20℃; under 750.075 Torr; for 2h;	To a solution of 4,4-dimethyl-cyclohex-2-enone (50 g, 403 mmol) in EA (230 ml_) a suspension of Pd/C (2.5 g, 10% Pd) in EA is added. The suspension is stirred at rt for 2 h under 1 bar H2. The catalyst is filtered off and the solvent of the filtrate is carefully evaporated to give 4,4-dimethyl-cyclohexanone (50 g) as a colourless oil which slowly crystallizes; 1H NMR (CDCI3): delta 2.34 (t, J = 6.4 Hz, 4H), 1.66 (t, J = 6.4 Hz, 4H), 1.09 (s, 6H).
	palladium-carbon; In ethyl acetate;	Step 1: 4,4-Dimethylcyclohexanone A mixture of 4,4-dimethyl-2-cyclohexene-1-one (5.5 g) and 10% Pd/C (0.25 g, wet, Degussa type E101) in EtOAc (50 mL) was hydrogenated under 15 psi for 3 h at room temperature. The mixture was filtered through Celite and the filtrate was concentrated in vacuo affording the title compound as a colorless solid. 1H NMR (400 MHz, CDCl3) delta ppm 1.07 (s, 6H), 1.65 (t, J=7 Hz, 4H), 2.35 (t, J=7 Hz, 4H).
	With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20℃; under 775.743 Torr; for 3h;	A mixture of 4,4-dimethyl-2-cyclohexene-1-one (5.5 g) and 10% Pd/C (0.25 g, wet, Degussa type E101) in EtOAc (50 mL) was hydrogenated under 15 psi for 3 h at room temperature. The mixture was filtered through Celite and the filtrate was concentrated in vacuo affording the title compound as a colorless solid.
	With hydrogen;5%-palladium/activated carbon; In ethyl acetate; at 20℃; under 760.051 Torr; for 2h;	Step A: 4,4-Dimethyl-cyclohexanone 1 g of 5% Pd/C is added in portions to a solution of 4,4-dimethyl-2-cyclohexen-1-one (0.0805 mol, 10.6 ml) in 110 ml of AcOEt, and then the whole is stirred for 2 hours at ambient temperature under atmospheric hydrogen pressure. The palladium is removed by filtration and concentration to dryness is carried out. The resulting oil crystallises gradually. The title compound is thus obtained in the form of a white solid.

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3
[ 1073-13-8 ]
[ 932-01-4 ]
[ 5020-09-7 ]
[ 4255-62-3 ]

Reference： [1]Tetrahedron,1980,vol. 36,p. 1937 - 1942
[2]European Journal of Organic Chemistry,2000,p. 1793 - 1797

4
[ 34270-90-1 ]
[ 4255-62-3 ]
[ 97827-52-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In tetrahydrofuran; at 65℃; for 2h;Reflux;	Step 1 :NaH (60% in oil, 975 mg, 24.38 mmol) is washed with pentane (3x) and then suspended in dry THF (10 mL). A solution of 4,4-dimethyl cyclohexanone (1.02 g, 8.12 mmol, Combi-Blocks) in THF (5 mL) is added, followed by bis-2-iodoethyl ether (1.25 mL, 8.80 mmol). The reaction mixture is heated to 65C. When an exothermic reaction occurs, external heating is stopped and the reaction mixture is stirred for 1.5 h. The reaction mixture is heated at reflux for 30 min, and then is poured into water and extracted with ether. The aqueous phase is acidified to pH 6 with 1 M HCI and extracted with ether (2x). The filtrate is dried over anhydrous Na2S04, concentrated under reduced pressure and purified by Combiflash (90:10Hex EtOAc) to afford 6a1.

Reference： [1]Tetrahedron,1987,vol. 43,p. 5677 - 5684
[2]Journal of the American Chemical Society,1985,vol. 107,p. 5289 - 5290
[3]Patent: WO2013/26163,2013,A1 .Location in patent: Page/Page column 36-37

5
[ 4255-62-3 ]
[ 616-38-6 ]
[ 50388-51-7 ]

Yield	Reaction Conditions	Operation in experiment
84%		Example 8 l-(2-(bromomethyl)-4,4-dimethylcyclohex-l-enyl)-4-chlorobe?zene <n="44"/>xi fTo a solution of 21 g of dimethyl carbonate (0.23 mol) in dry THF (400 ml) was added sodium hydride (9.6 g, 0.24 mol) by portion at 0 0C. The resulting mixture was stirred at 0 0C for 30 min and then was added a solution of 10 g of compound a (79 mmol) in THF (100 ml) dropwise over 30min. The resultant mixture was heated to 600C - 800C for 3h before cooled to room temperature. The reaction mixture was poured into saturated NaHCO3 solution and extracted with ether. The organic layer was washed with water, brine, dried over Na2SO4 and concentrated to give 25 g of of intermediate b methyl 5,5-dimethyl-2-oxocyclohexanecarboxylate (yield: 84%). MS (ESI) m/e (M+H+): 185.
84%		Example 3Preparation of 1 N- { 1- [ 4- (4 ' -Chloro-biphenyl-2-ylmethyl) - piperazin-1-yl] -quinazolin-4-yl}-4- ( (R) -3-dimethylamino-l- phenylsulfanylmethyl-propylamino) -3-nitro-benzenesulfonamide To a solution of 21 g of dimethyl carbonate (0.23 mol) in dry THF (400 ml) was added sodium hydride (9.6 g, 0.24 mol) by portion at 0 0C. The resulting mixture was stirred at 0 0C for 30 min and then was added a solution of 10 g of compound a (79 mmol) in THF (100 ml) dropwise over 30min. The resultant mixture was heated to 60 0C - 80 0C for 3h before cooled to room temperature. The reaction mixture was poured into saturated NaHCtheta3 solution and extracted with ether. The organic layer was washed with water, brine, dried over Na2SO4 and concentrated to give 25 g of of intermediate b methyl 5, 5-dimethyl-2- oxocyclohexanecarboxylate (yield: 84%) . MS (ESI) m/e (M+H+) : 185.
		Example 9A methyl 5,5-dimethyl-2-oxocyclohexanecarboxylate To a suspension of hexane-washed NaH (0.72 g, 60%, 18 mmol) in tetrahydrofuran (30 mL) was added a solution of 4,4-dimethylcyclohexanone (2.0 g, 15.6 mmol) in tetrahydrofuran (20 mL). The suspension was stirred at room temperature for 30 minutes. Then dimethylcarbonate (6.31 mL, 75 mmol) was added dropwise by syringe. The mixture was heated to reflux for four hours. The mixture was acidified with 5% HCl and extracted with dichloromethane (100 mL*3) and washed with water, brine, and dried over Na2SO4. After concentration, the crude product was loaded on a column and eluted with 10% ethyl acetate in hexane to give title compound.

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 2548 - 2559
[2]Canadian Journal of Chemistry,1988,vol. 66,p. 2345 - 2347
[3]Canadian Journal of Chemistry,1997,vol. 75,p. 742 - 753
[4]Patent: WO2008/61208,2008,A2 .Location in patent: Page/Page column 42-43
[5]Patent: WO2009/143246,2009,A2 .Location in patent: Page/Page column 210
[6]Journal of Medicinal Chemistry,2016,vol. 59,p. 9431 - 9442
[7]Journal of Organic Chemistry,1981,vol. 46,p. 5434 - 5436
[8]Angewandte Chemie - International Edition,2003,vol. 42,p. 2785 - 2788
[9]Patent: US2010/184766,2010,A1 .Location in patent: Page/Page column 46

6
[ 4255-62-3 ]
[ 932-01-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2365 - 2369
[2]Bulletin des Societes Chimiques Belges,1980,vol. 89,p. 389 - 398
[3]Journal of the American Chemical Society,1968,vol. 90,p. 6486 - 6492
[4]Journal of the American Chemical Society,2009,vol. 131,p. 251 - 262
[5]Organic and Biomolecular Chemistry,2012,vol. 10,p. 7321 - 7326

7
[ 4255-62-3 ]
[ 121148-01-4 ]
[ 1002728-77-9 ]

Yield	Reaction Conditions	Operation in experiment
75%		Step A: methyl-r2S.4SVl-BOC-4-rr4.4-dimethylcyclohexyl')aminol pyrrolidine- 2-carboxylate; [579] To methyl (2S,4S)-l-Boc-4-aminopyrrolidine-2-carboxylate (1.07 g, 4.38 mmol) and dimethylcyclohexanone (0.66g, 5.25 mmol) in DCE (20 mL) was added dropwise NaBH(OAc) (1.39 g, 6.57 mmol) at it. The reaction mixture was stirred at it for 4 h, a saturated NaHCO aqueous solution was added, and extracted with DCM (50 mL X 2) and EtOAc. The organic extracts were washed with brine, dried over MgSO 4 , filtered, and concentrated in vacuo. The obtained residue was purified by column chromatography (eluent, EtO Ac/Hex = 1/2) to give the title compound (1.16 g, 75 %).[580] MS[M+H] = 355(M+1)
75%	With acetic anhydride; In 1,2-dichloro-ethane; at 20℃; for 4h;	Methyl(2S,4S)-1-Boc-4-aminopyrrolidine-2-carboxylate (1.07 g, 4.38 mmol) obtained in Preparation 1 and 4,4-dimethylcyclohexanone (0.66 g, 5.25 mmol) were dissolved in DCE (10 ml), and NaBH(OAc)3 (1.39 g, 6.57 mmol) was added thereto at room temperature. After the reaction mixture was stirred at room temperature for 4 hours, the organic extracts were extracted with a saturated NaHCO3 aqueous solution. The extracted organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The obtained residue was purified by column chromatography (eluent: EtOAc/Hex=1/2) to give the title compound (1.16 g, 75%).MS [M+H]=355 (M+1)
75%	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 4h;	Example 1: N-{(3 S £ S )-l-[(3 S ,4 R )-l- tert - butyl-4-(4-chlorophenyl)pyrrolidin-3-yl]carbonyl}-5-[(4-methylpiperazin-l-yl)car bonyl]pyrrolidin-3-yl}- N -(4,4-dimethylcyclohexyl)acetamide TFA salt[461] TFA salt of[462][463] Step A: Methyl (2 S .4 S s)-l-BOC-4-[(4.4-dimethylcvclohexyls)amino1pyrrolidine-2-carboxylate[464] Methyl (2S,4S)-l-Boc-4-aminopyrrolidine-2-carboxylate (1.07 g, 4.38 mmol) obtained in Preparation 1 and 4,4-dimethylcyclohexanone(0.66 g, 5.25 mmol) were dissolved in DCE (10 ml), and NaBH(OAc)3 (1.39 g, 6.57 mmol) was added thereto at room temperature. After the reaction mixture was stirred at room temperature for 4 hours, the organic extracts were extracted with a saturated NaHCO3 aqueous solution. The extracted organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The obtained residue was purified by column chromatography (eluent: EtOAc/ Hex = 1/2) to give the title compound (1.16 g, 75 %).[465] MS [M+H] = 355 (M+ 1)

Reference： [1]Patent: WO2008/7930,2008,A1 .Location in patent: Page/Page column 34
[2]Patent: US2010/120783,2010,A1 .Location in patent: Page/Page column 14
[3]Patent: WO2010/56022,2010,A2 .Location in patent: Page/Page column 32

8
[ 24589-77-3 ]
[ 4255-62-3 ]
[ 1007568-11-7 ]

Yield	Reaction Conditions	Operation in experiment
	In acetic acid;Heating / reflux;	A sample of 4-hydrazino benzoic acid hydrochloride (0.75g, 4 mmol), 4,4- dimethyl cyclo hexanone (0.505g, 4 mmol), were taken in 6 ml of AcOH and the mixture was refluxed overnight. The mixture was cooled to room temperature and kept in refrigerator for 2 hrs. The solidified mixture was suspended in CH2Cl2 (10 ml), filtered and washed with CH2Cl2 to obtain 0.85 g of the product. 1U NMR 500 MHz D6DMSO: 12.21, s, IH, 11.08, s, IH, 7.98, d, J=0.9, IH,7.62, dd, J=1.6, 8.5, IH, 7.28, d, J=8.4, IH, 2.69, t, J=6.3, 2H, 2.45, s, 2H, 1.61, t, J=6.4, 2H, 1.01, s, 6H.
	In acetic acid;Reflux;	A sample of <strong>[24589-77-3]4-hydrazinobenzoic acid hydrochloride</strong> (0.75g, 4 mmol), 4,4- dimethyl cyclohexanone (0.505g, 4 mmol), were taken in 6 ml of AcOH and the mixture was refluxed overnight. The mixture was cooled to room temperature and kept in refrigerator for 2 hrs. The solidified mixture was suspended in CH2Cl2 (10 ml), filtered and washed with CH2Cl2 to obtain 0.85 g of the product. 1H NMR 500 MHz D6-DMSO: 12.21, s, IH, 11.08, s, IH, 7.98, d, J=0.9, IH, 7.62, dd, J=I.6, 8.5, IH, 7.28, d, J=8.4, IH, 2.69, t, J=6.3, 2H, 2.45, s, 2H, 1.61, t, 3=6 lambda, 2H, 1.01, s, 6H.

Reference： [1]Patent: WO2008/21745,2008,A2 .Location in patent: Page/Page column 83
[2]Patent: WO2009/103022,2009,A1 .Location in patent: Page/Page column 31

9
[ 52068-30-1 ]
[ 4255-62-3 ]
1,2,3,4-tetrahydro-3,3-dimethyl-6-phenylmethoxy-9H-dibenzo[b,d]pyrrole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.3 g (90.2%)	In acetic acid;	EXAMPLE 59 Preparation of 1,2,3,4-tetrahydro-3,3-dimethyl-6-phenylmethoxy-9H-dibenzo[b,d]pyrrole Using the procedure of Example 1,4.5 g of <strong>[52068-30-1]4-benzyloxyphenylhydrazine hydrochloride</strong> was reacted with 8.9 g of 4,4-dimethylcyclohexanone in 100 ml of 80percent aqueous acetic acid to give 4.3 g (90.2percent) of 1,2,3,4-tetrahydro-3,3-dimethyl-6-phenylmethoxy-9H-dibenzo[b,d]pyrrole as a tan solid after purification with activated carbon (Darco G-60) and repeated crystallizations.

Reference： [1]Patent: US5451600,1995,A

10
[ 4255-62-3 ]
[ 254881-77-1 ]
[ 1226771-75-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 4h;	Step A: Methyl (2 R Lambda S s)-l-BOC-4-[(4.4-dimethylcvclohexyls)aminolpyrrolidine-2-carboxylate[642] Methyl (2/?,4S)-l-Boc-4-aminopyrrolidine-2-carboxylate (1.07 g, 4.38 mmol) obtained in Preparation 2 and 4,4-dimethylcyclohexanone (0.66 g, 5.25 mmol) were dissolved in DCE (20 mL) and NaBH(OAc)3 (1.39 g, 6.57 mmol) was added thereto at room temperature. The reaction solution was stirred for 4 hours at room temperature and was extracted with DCM (50 mL X 2) and EtOAc. The extracted organic solution was washed with brine, dried over MgSO4, filterated and concentrated in vacuo. The obtained residue was purified by column chromatography (eluent, EtO Ac/Hex = 1/2) to give the title compound (1.16 g, 75 %). [643] MS[M+H] = 355 (M+ 1) [644]
	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 4h;	Methyl(2R,4S)-1-Boc-4-aminopyrrolidine-2-carboxylate (1.07 g, 4.38 mmol) obtained in Preparation 2 and 4,4-dimethylcyclohexanone (0.66 g, 5.25 mmol) were dissolved in DCE (20 mL) and NaBH(OAc)3 (1.39 g, 6.57 mmol) was added thereto at room temperature. The reaction solution was stirred for 4 hours at room temperature and was extracted with DCM (50 mL×2) and EtOAc. The extracted organic solution was washed with brine, dried over MgSO4, filterated and concentrated in vacuo. The obtained residue was purified by column chromatography (eluent, EtOAc/Hex=1/2) to give the title compound (1.16 g, 75 N.MS[M+H]=355 (M+1)

Reference： [1]Patent: WO2010/56022,2010,A2 .Location in patent: Page/Page column 47-48
[2]Patent: US2010/120783,2010,A1 .Location in patent: Page/Page column 21

11
[ 4255-62-3 ]
[ 25834-99-5 ]

Reference： [1]Patent: US2011/124559,2011,A1
[2]Journal of the American Chemical Society,2011,vol. 133,p. 13844 - 13847

12
[ 33670-32-5 ]
[ 4255-62-3 ]
[ 64416-07-5 ]

Yield	Reaction Conditions	Operation in experiment
		An oven-dried 500 mL one- necked round bottomed flask was charged with (methoxymethyl)triphenylphosphonium bromide (22.4 g, 65.4 mmol) and dry THF (40 mL) and then cooled to -78 C. To this solution was added w-BuLi (2.8 M in hexane, 23.3 mL, 65.4 mmol) over 10 min by syringe. The resultant red ylide solution was then warmed to rt, stirred for 3 hours, and cooled to -78 C. To this ylide solution was added 4-dimethyl-cyclohexanone (5.5 g, 43.6 mmol) in dry THF (5 mL) via syringe over 10 min. After being stirred for 1 hour at -78 C, the reaction mixture was warmed to rt slowly and stirred for 10 hours. After that the reaction mixture was cooled to 0 C, quenched with aq.NaHC03 (60 mL), and extracted with ether (3 x 60 mL). The organic layer was washed with brine (60 mL) and dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica chromatography using hexane-Et20 isocratic 20% as eluant to give the title compound as clear oil. 1H NMR (400 MHz, CDC13) delta 5.75 (bs, 1H), 3.75 (s, 3H), 2.18 (ddd, J = 12.8, 6.4, 1.2 Hz, 2H), 1.95 (ddd, J = 12.8, 6.4, 1.2 Hz, 2H), 1.27 (ddd, J = 12.8, 6.8, 2.0 Hz, 4H), 0.91 (s, 6H). No ionization by LCMS.

Reference： [1]Patent: WO2012/87519,2012,A1 .Location in patent: Page/Page column 94; 95

13
[ 4255-62-3 ]
[ 86847-59-8 ]
[ 1397287-46-5 ]

Yield	Reaction Conditions	Operation in experiment
57%		To a solution of N-(pyridin-2-yl)pivalamide (1.1 g, 6 mmol) in tetrahydrofurane (30 mL) was added at -78 C. under nitrogen and stirring a solution of 1.6M n-butyllithium in hexane (7.88 mL, 12.6 mmol). The reaction is exotherm and it turns light yellow. The reaction was stirred for 15 minutes at -78 C. and then for 2 hours at 0 C. The reaction was cooled to -78 C. and 4,4-dimethylcyclohexanone (937 mg, 7.2 mmol) dissolved in tetrahydrofurane (5 mL) was added dropwise. The reaction was warmed to room temperature over night. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate as the eluent to yield the title compound as a white powder (1.034 g, 57%).MS ISP (m/e): 305.3 (15) [(M+H)+], 287.3 (93), 327.3 (100).
57%		a) N-(3-(l-Hydroxy-4,4-dimethylcyclohexyl)pyridin-2-yl)pivalamideTo a solution of N-(pyridin-2-yl)pivalamide (1.1 g, 6 mmol) in tetrahydrofurane (30 mL) was added at -78C under nitrogen and stirring a solution of 1.6M n-butyllithium in hexane (7.88 mL, 12.6 mmol). The reaction is exotherm and it turns light yellow. The reaction was stirred for 15 minutes at -78Ca nd then for 2 hours at 0C. The reaction was cooled to -78C and 4,4- dimethylcyclohexanone (937 mg, 7.2 mmol) dissolved in tetrahydrofurane (5 mL) was added dropwise. The reaction was warmed to room temperature over night. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate as the eluent to yield the title compound as a white powder (1.034 g, 57 %).MS ISP (m/e): 305.3 (15) [(M+H)+], 287.3 (93), 327.3 (100).

Reference： [1]Patent: US2012/225884,2012,A1 .Location in patent: Page/Page column 23
[2]Patent: WO2012/116965,2012,A1 .Location in patent: Page/Page column 49

14
[ 897365-76-3 ]
[ 4255-62-3 ]
[ 282735-66-4 ]
(3'S,4'R,7'S,8'S,8a'R)-6-chloro-8'-(3-chloro-2-fluorophenyl)-4,4-dimethyl-3',4'-diphenyl-3',4',8',8a'-tetrahydro-1'H-dispiro[cyclohexane-1,6'-pyrrolo[2,1-c][1,4]oxazine-7',3-indole]-1',2(1H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%	In toluene; at 70℃; for 120h;Molecular sieve; Inert atmosphere;	<strong>[282735-66-4](5R,6S)-5,6-diphenylmorpholin-2-one</strong> (506 mg, 2.00 mmol), 4,4-dimethylcyclohexanone (252 mg, 2.00 mmol), and molecular sieves 4A (powder) (2 g) were added to a toluene (20 ml) solution of (3E/Z)-6-chloro-3-(3-chloro-2-fluorobenzylidene)-1,3-dihydro-2H-indol-2-one (WO2006/091646) (616 mg, 2.00 mmol) under nitrogen atmosphere and the resulting mixture was stirred under heating at 70 C. for 5 days. After cooling, insoluble matter was removed by filtration through celite and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the organic layer was washed with 1N hydrochloric acid and brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=9:1?6:1 (v/v)] to give 194 mg (14%) of the title compound as a yellow amorphous solid.1H-NMR (400 MHz, CDCl3) S: 0.19 (3H, s), 0.52 (3H, s), 0.94-1.00 (3H, m), 1.29-1.41 (3H, m), 1.80 (1H, d, J=11.0 Hz), 2.27 (1H, d, J=14.2 Hz), 4.61 (1H, d, J=11.0 Hz), 4.86 (1H, d, J=2.7 Hz), 5.35 (1H, d, J=11.4 Hz), 6.23 (1H, d, J=8.2 Hz), 6.60 (1H, dd, J=8.2, 1.8 Hz), 6.72-6.78 (2H, m), 6.88 (1H, d, J=1.8 Hz), 7.07-7.26 (11H, m), 7.67 (1H, s), 7.77 (1H, t, J=6.4 Hz).

Reference： [1]Patent: US2012/264738,2012,A1 .Location in patent: Page/Page column 17

15
[ 1360821-96-0 ]
[ 4255-62-3 ]
[ 282735-66-4 ]
(3'S,4'R,7'S,8'S,8a'R)-6-chloro-8'-(3-chloro-2-fluorophenyl)-4,4-dimethyl-3',4'-diphenyl-3',4',8',8a'-tetrahydro-1'H-dispiro[cyclohexane-1,6'-pyrrolo[2,1-c][1,4]oxazine-7',3-pyrrolo[2,3-b]pyridine]-1',2(1H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper(II) sulfate; In toluene; for 24h;Reflux; Inert atmosphere;	<strong>[282735-66-4](5R,6S)-5,6-diphenylmorpholin-2-one</strong> (2.62 g, 10.3 mmol), 4,4-dimethylcyclohexanone (1.30 g, 10.3 mmol), and anhydrous copper sulfate (16.4 g, 103 mmol) were added to a toluene (80 ml) solution of the compound (2.67 g, 8.60 mmol) obtained in Reference Example 1 and the resulting mixture was heated to reflux for 24 hours under nitrogen atmosphere. After cooling, insoluble matter was removed by filtration through celite and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the organic layer was washed with 1N hydrochloric acid solution and brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=9:1?6:1 (v/v)] to give 5.1 g (90%) of the title compound as a yellow amorphous solid.1H-NMR (400 MHz, CDCl3) delta: 0.20 (3H, s), 0.55 (3H, s), 0.90-1.08 (3H, m), 1.21-1.32 (1H, m), 1.33-1.47 (2H, m), 1.76-1.86 (1H, m), 2.26-2.36 (1H, m), 4.65 (1H, d, J=11.2 Hz), 4.88 (1H, d, J=3.2 Hz), 5.36 (1H, d, J=11.2 Hz), 6.52 (1H, d, J=7.8 Hz), 6.64 (1H, d, J=8.2 Hz), 6.71-6.78 (2H, m), 7.06-7.24 (10H, m), 7.25-7.32 (1H, m), 7.74-7.83 (1H, m), 9.00 (1H, s).

Reference： [1]Patent: US2012/264738,2012,A1 .Location in patent: Page/Page column 18

16
[ 1398569-83-9 ]
[ 4255-62-3 ]
[ 282735-66-4 ]
(3'S,4'R,7'S,8'R,8a'R)-6-chloro-8'-(2-chloropyridin-4-yl)-4,4-dimethyl-3',4'-diphenyl-3',4',8',8a'-tetrahydro-1'H-dispiro[cyclohexane-1,6'-pyrrolo[2,1-c][1,4]oxazine-7',3-indole]-1',2(1H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With boron trifluoride diethyl etherate; In tetrahydrofuran; at 70℃; for 168h;Molecular sieve; Inert atmosphere;	A boron trifluoride-diethyl ether complex (0.038 ml, 0.30 mmol) and molecular sieves 4A (powder) (3 g) were added to a tetrahydrofuran (30 ml) solution of the compound (873 mg, 3.00 mmol) obtained in Reference Example 4, <strong>[282735-66-4](5R,6S)-5,6-diphenylmorpholin-2-one</strong> (760 mg, 3.00 mmol), and 4,4-dimethylcyclohexanone (379 mg, 3.00 mmol) under nitrogen atmosphere and the resulting mixture was stirred under heating at 70 C. for 7 days. After cooling, insoluble matter was removed by filtration through celite and the filtrate was washed with brine and then dried over anhydrous sodium sulfate.The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=4:1?1:1 (v/v)] to give 1.18 g (60%) of the title compound as a pale yellow amorphous solid.1H-NMR (400 MHz, CDCl3) delta: 0.54 (3H, s), 0.67 (3H, s), 0.80-0.92 (1H, m), 1.15-1.41 (4H, m), 1.71-1.82 (1H, m), 1.82-1.94 (1H, m), 2.15-2.26 (1H, m), 4.42 (1H, d, J=10.7 Hz), 4.81 (1H, d, J=3.7 Hz), 5.03 (1H, d, J=10.7 Hz), 6.60-6.68 (2H, m), 6.78-6.84 (2H, m), 6.85-6.89 (1H, m), 6.91-6.98 (2H, m), 7.06-7.31 (9H, m), 7.47 (1H, s), 8.14 (1H, d, J=5.1 Hz).

Reference： [1]Patent: US2012/264738,2012,A1 .Location in patent: Page/Page column 23

17
[ 623-73-4 ]
[ 4255-62-3 ]
[ 1423716-54-4 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 7555 - 7560

18
[ 4255-62-3 ]
[ 20615-18-3 ]

Yield	Reaction Conditions	Operation in experiment
83%Chromat.	With ammonium hydroxide; nickel-aluminum alloy; water; at 20℃; for 2.5h;Sonication; Green chemistry;	General procedure: Ni-Al alloy (200 mg) and cyclohexanone (35 muL, 0.34 mmol) were suspended in 28?30percent NH4OH (3 mL) and sonicated (Branson 1510MTH ultrasonic bath) for 2 h. After the completion of the reaction, the excess alloy and solid by-products were removed by filtration. The filtrate was extracted with EtOAc (2 × 2 mL). The organic extracts were combined and dried over anhyd Na2SO4. The solvent was removed in vacuo and the crude product was purified by flash chromatography.

Reference： [1]Patent: WO2014/37900,2014,A1
[2]Synthesis,2016,vol. 48,p. 3127 - 3133

19
[ 4255-62-3 ]
[ 1423716-54-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 5714 - 5727

20
[ 1398569-88-4 ]
[ 4255-62-3 ]
[ 282735-66-4 ]
(3'S,4'R,7'S,8'S,8a'R)-6-chloro-8'-(2-chloro-3-fluoropyridin-4-yl)-4,4-dimethyl-3',4'-diphenyl-3',4',8',8a'-tetrahydro-1'H-dispiro[cyclohexane-1,6'-pyrrolo[2,1-c][1,4]oxazine-7',3-indole]-1',2(1H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With boron trifluoride diethyl etherate; In tetrahydrofuran; at 70℃; for 168h;Molecular sieve; Inert atmosphere;	[Step 2] (3'S,4'R,7'S,8'S,8a'R)-6'-chloro-8'-(2-chloro-3-fluoropyridin-4-yl)-4,4-dimethyl-3',4'-diphenyl-3',4',8',8a'-tetrahydro-1'H-dispiro[cyclohexane-1,6'-pyrrolo[2,1-c][1,4]oxazine-7',3'-indole]-1',2'(1'H)-dione A boron trifluoride-diethyl ether complex (0.15 ml, 1.20 mmol) and 4A molecular sieves (powder) (3 g) were added to a tetrahydrofuran (30 ml) solution of the compound (1.86 g, 6.00 mmol) obtained in Step 1, <strong>[282735-66-4](5R,6S)-5,6-diphenylmorpholin-2-one</strong> (1.67 g, 6.60 mmol), and 4,4-dimethylcyclohexanone (0.83 g, 6.60 mmol) under a nitrogen atmosphere and the resulting mixture was stirred under heating at 70C for 7 days. After cooling, insoluble matter was removed by filtration through celite and the filtrate was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [n-hexane:ethyl acetate = 4:1 ? 1:1 (v/v)] to give 3.39 g (84%) of the title compound as a solid. 1H-NMR (400 MHz, CDCl3) delta: 0.21 (3H, s), 0.53 (3H, s), 0.89-1.08 (3H, m), 1.28-1.43 (3H, m), 1.73-1.81 (1H, m), 2.23-2.33 (1H, m), 4.58 (1H, d, J=11.0 Hz), 4.86 (1H, d, J=3.2 Hz), 5.31 (1H, d, J=11.0 Hz), 6.25 (1H, d, J=8.3 Hz), 6.67 (1H, dd, J=8.3, 1.8 Hz), 6.72-6.77 (2H, m), 6.93 (1H, d, J=1.8 Hz), 7.04-7.17 (6H, m), 7.18-7.25 (3H, m), 7.79 (1H, t, J=4.6 Hz), 7.99 (1H, s), 8.29 (1H, d, J=5.0 Hz). MS (APCI) m/z: 670 (M+H)+.

Reference： [1]Patent: EP2894156,2015,A1 .Location in patent: Paragraph 0084

21
[ 590-66-9 ]
[ 2979-19-3 ]
[ 1193-46-0 ]
[ 932-01-4 ]
[ 767-12-4 ]
[ 1193-47-1 ]
[ 4255-62-3 ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 15833 - 15842

22
[ 1398569-88-4 ]
[ 4255-62-3 ]
[ 282735-66-4 ]
(3'S,4'R,7'S,8'S,8a'R)-6"-chloro-8'-(2-chloro-3-fluoropyridin-4-yl)-4,4-dimethyl-3',4'-diphenyl-3',4',8',8a'-tetrahydro-1'H-dispiro[cyclohexane-1,6'-pyrrolo[2,1-c][1,4]oxazine-7',3"-indole]-1',2"(1"H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With boron trifluoride diethyl etherate; In tetrahydrofuran; at 70℃; for 168h;Molecular sieve; Inert atmosphere;	A boron trifluoride-diethyl ether complex (0.15 ml, 1.20 mmol) and 4A molecular sieves (powder) (3 g) were added toa tetrahydroffiran (30 ml) solution of the compound (1.86 g, 6.00 mmol) obtained in Step 1, (5R,65)-5,6-diphenylmor- pholin-2-one (1.67 g, 6.60 mmol), and 4,4-dimethylcyclo- hexanone (0.83 g, 6.60 mmol) under a nitrogen atmosphere and the resulting mixture was stirred under heating at 70 C.for 7 days. After cooling, insoluble matter was removed by filtration through celite and the filtrate was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=4: 1 -4 1:1 (v/v)] to give 3.39 g (84%) of the title compound as a solid.?H-NMR (400 MHz, CDC13) oe: 0.21 (3H, s), 0.53 (3H, s),0.89-1.08 (3H, m), 1.28-1.43 (3H, m), 1.73-1.81 (1H, m),2.23-2.33 (1H, m), 4.58 (1H, d, J=1 1.0Hz), 4.86 (1H, d, J=3.2Hz), 5.31 (1H, d, J=11.0 Hz), 6.25 (1H, d, J=8.3 Hz), 6.67(1H, dd, J=8.3, 1.8Hz), 6.72-6.77 (2H, m), 6.93 (1H, d, J=1 .8Hz), 7.04-7.17 (6H, m), 7.18-7.25 (3H, m), 7.79 (1H, t, J=4.6 Hz), 7.99 (1H, s), 8.29 (1H, d, J=5.0 Hz).MS (APCI) mlz: 670 (M+H).

Reference： [1]Patent: US9359368,2016,B2 .Location in patent: Page/Page column 19; 20

23
[ 908027-64-5 ]
[ 4255-62-3 ]
[ 282735-66-4 ]
(3'S,4'R,7'S,8'S,8a'R)-6"-chloro-8'-(3-chloro-2-fluorophenyl)-4,4-dimethyl-3',4'-diphenyl-3',4',8',8a'-tetrahydro-1'H-dispiro[cyclohexane-1,6'-pyrrolo[2,1-c][1,4]oxazine-7',3"-indole]-1',2"(1"H)-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 2819 - 2839

24
[ 4255-62-3 ]
[ 1044598-91-5 ]

Reference： [1]Patent: WO2017/101851,2017,A1
[2]Patent: WO2017/123616,2017,A1

25
[ 16182-15-3 ]
[ 4255-62-3 ]
C₁₇H₂₆N₂O₂S [ No CAS ]

Reference： [1]Organic Syntheses,1997,vol. 74,p. 217 - 217

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Precautionary Statements-General
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P321
P322
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P342	If experiencing respiratory symptoms:
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P351	Rinse cautiously with water for several minutes.
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P362	Take off contaminated clothing and wash before reuse.
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P378
P380	Evacuate area.
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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
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Physical hazards
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H200	Unstable explosive
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H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
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H221	Flammable gas
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H223	Flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H290	May be corrosive to metals
Health hazards
Code	Phrase
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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H310	Fatal in contact with skin
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H317	May cause an allergic skin reaction
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H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
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. 4255-62-3 ]

Quality Control of [ 4255-62-3 ]

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[ 4255-62-3 ] Synthesis Path-Upstream 1~6

[ 4255-62-3 ] Synthesis Path-Downstream 1~25

Related Functional Groups of [ 4255-62-3 ]

Aliphatic Cyclic Hydrocarbons

Ketones

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[ 4255-62-3 ]