Name: 14381-42-1|1-Indanecarboxylic acid|98%
Brand: Ambeed
SKU: A212118
Price: 8.0 USD
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1
[ 67-56-1 ]
[ 14381-42-1 ]
[ 26452-96-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: Indan-1-carboxylic acid With sulfuryl dichloride In dichloromethane at 20℃; for 0.583333h; Stage #2: methanol In dichloromethane at 20℃; for 3h;	3.A Step A: Thionyl Chloride (0.95 mL, 13.0 mmol) was added to a room temperature solution of indane-1-carboxylic acid dissolved in 20 mL of dichloromethane. The reaction mixture was stirred at room temperature for 35 minutes after which time the volume was reduced by approximately 50% via a rotovap. Then 20 mL of methanol was added and the reaction was stirred at room temperature for 3 hours, Evaporation of the solvent and column chromatography (9/1 hexanes/EtOAc) afforded of methyl indane-1-carboxylate (2.2 g, 100%) as a colorless oil.
91%	Stage #1: Indan-1-carboxylic acid With thionyl chloride In dichloromethane at 20 - 30℃; for 1h; Stage #2: methanol In dichloromethane at 20 - 30℃; for 3h;	2.1 Step 1 (0284) Methyl 2,3-dihydro- 1 //-indene- 1 -carboxyl ate 2b A dried round-bottom flask was charged with 2, 3 -dihydro- IH- indene- 1 -carboxylic acid 2a (10.0 g, 61.66 mmol) and DCM (100 mL), followed by addition of SOCh (6.7 mL, 92.49 mmol) at room temperature. The reaction mixture was stirred at room temperature for lh, then concentrated to half volume by rotavapor. To the reaction mixture above was added MeOH (100 mL) slowly and the reaction was continued to stir at room temperature for 3h. Then the mixture was concentrated by rotavapor and purified by column chromatography on silica-gel with 0-25% EtOAc in hexane as eluent on the TELEDYNE ISCO system to give the desired product 2b as colorless oil (9.85 g, yield: 91%), MS (ESI): m/z =177 [M + 1].
91%	Stage #1: Indan-1-carboxylic acid With thionyl chloride In dichloromethane at 20℃; for 1h; Stage #2: methanol In dichloromethane at 20℃; for 3h;	1.1 Methyl 2,3-dihydro- 1 //-indene- 1 -carhoxylate lb A dried round-bottom flask was charged with 2,3-dihydro- 1 /-indene- 1 -carboxylic acid la (10.0 g, 61.66 mmol) and DCM (100 mL), followed by addition of SOCh (6.7 mL, 92.49 mmol) at room temperature. The reaction mixture was stirred at room temperature for lh, then concentrated to half volume by rotavapor. To the reaction mixture above was added MeOH (100 mL) slowly and the reaction was continued to stir at room temperature for 3h. Then the mixture was concentrated by rotavapor and purified by column chromatography on silica-gel with 0-25% EtOAc in hexane as eluent on the TELEDYNE ISCO system to give the desired product lb as colorless oil (9.85 g, yield: 91%), MS (ESI): m/z =177 [M + 1].

	With sulfuric acid
	With thionyl chloride for 2h; Thermolysis;

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/108550, 2009, A1 Location in patent: Page/Page column 31
[2]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - WO2020/47082, 2020, A1 Location in patent: Page/Page column 42
[3]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - WO2020/205538, 2020, A1 Location in patent: Page/Page column 28-29
[4]Wunderlich [Archiv der Pharmazie, 1953, vol. 286, p. 512,515]
[5]Ranade, Vidyadhar S.; Consiglio, Giambattista; Prins, Roel [Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1132 - 1138]

2
[ 14209-41-7 ]
[ 14381-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium 10% on activated carbon; In ethanol; for 1h;	Indan-1-carboxylic acid 4-nitro-benzyI ester:; To a solution of 3H-Indene-l-carboxylic acid (2.0 g, 13.3 mmol) in ethanol (35 mL) was added 10% Pd/C (200 mg). The reaction mixture was stirred under an H2 atmosphere for Ih. The mixture was filtered through Celite and concentrated in vacuo. The residue was combined withjp-nitrobenzyl bromide (5.8 g, 26.8 mmoles) and l,8-diazabicyclo[5.4.0]undec-7-ene (2.4 mL, 16.0 mmol) in 65 mL of benzene, and was stirred at 5O0C for 20 hours. After this period the heterogeneous mixture was gravity filtered and the filtrate was evaporated in vacuo. The residue was combined with CH2Cl2 and was washed with IN HCl (2 x 25mL) and sat'd NaHCO3 (2 x 25mL), and the resulting CH2Cl2 solution was dried over anhydrous Na2SC^. The crude solid was purified using flash silica chromatography (0-10% EtOAc/Hexane) to yield 3.6 Ig (95%) of the intermediate. EPO <DP n="62"/>

Reference： [1]European Journal of Organic Chemistry,2009,p. 6217 - 6224
[2]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1920,vol. 170,p. 467
Bulletin de la Societe Chimique de France,1920,vol. <4> 27,p. 789
[3]Journal of Organic Chemistry,1942,vol. 7,p. 374,378
[4]Journal of Organic Chemistry,1965,vol. 30,p. 2948 - 2956
[5]Bulletin de la Societe Chimique de France,1964,p. 3076 - 3079
[6]Journal of Organic Chemistry,1961,vol. 26,p. 1375 - 1379
[7]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1551 - 1554
[8]Archiv der Pharmazie,1953,vol. 286,p. 512,515
[9]Journal of the South African Chemical Institute,1957,vol. 10,p. 5,10
[10]Patent: WO2006/55187,2006,A1 .Location in patent: Page/Page column 60
[11]Journal of the American Chemical Society,2020

3
[ 159496-97-6 ]
[ 14381-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	With barium dihydroxide; ethanol; silver nitrate
2.0 g	With jones' reagent In acetone at 0℃; for 1h;

Reference： [1]Tiffeneau; Orechow [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1920, vol. 170, p. 467][Bulletin de la Societe Chimique de France, 1920, vol. <4> 27, p. 789]
[2]Kato, Dai-Ichiro; Mitsuda, Satoshi; Ohta, Hiromichi [Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7234 - 7242]

4
[ 14381-42-1 ]
[ 19156-10-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With thionyl chloride In dichloromethane for 5h; Heating;
	With oxalyl dichloride In dichloromethane 1.) room temp., 1 h, 2.) reflux, 1 h;
	With thionyl chloride for 2.5h; Heating;

	With thionyl chloride
	With thionyl chloride In dichloromethane for 0.75h;
	With thionyl chloride Heating;
	With thionyl chloride at 40℃; for 0.333333h;
	With thionyl chloride for 2h; Reflux;
	With thionyl chloride for 3h; Reflux;
	With thionyl chloride for 2h; Reflux;
	With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;

Reference： [1]Sarges; Schnur; Belletire; Peterson [Journal of Medicinal Chemistry, 1988, vol. 31, # 1, p. 230 - 243]
[2]Clark, Robin D.; Weinhardt, Klaus K.; Berger, Jacob; Fisher, Lawrence E.; Brown, Christine M.; et al. [Journal of Medicinal Chemistry, 1990, vol. 33, # 2, p. 633 - 641]
[3]Lee-Ruff, Edward; Chung, Ying-Sheng [Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1551 - 1554]
[4]Vargha et al. [Acta Chimica Academiae Scientiarum Hungaricae, 1955, vol. 5, p. 111,114] Protiva et al. [Collection of Czechoslovak Chemical Communications, 1951, vol. 16/17, p. 331,341] Ray; Lahiri [Journal of the Indian Chemical Society, 1990, vol. 67, # 4, p. 324 - 326]
[5]Katz, Christopher E.; Aube, Jeffrey [Journal of the American Chemical Society, 2003, vol. 125, # 46, p. 13948 - 13949]
[6]Daum, Sebastian; Erdmann, Frank; Fischer, Gunter; De Lacroix, Boris Feaux; Hessamian-Alinejad, Anahita; Houben, Sabine; Frank, Walter; Braun, Manfred [Angewandte Chemie - International Edition, 2006, vol. 45, # 44, p. 7454 - 7458]
[7]Ranade, Vidyadhar S.; Consiglio, Giambattista; Prins, Roel [Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1132 - 1138]
[8]Jia, Yi-Xia; Kuendig, E. Peter [Angewandte Chemie - International Edition, 2009, vol. 48, # 9, p. 1636 - 1639]
[9]Dey, Chandan; Katayev, Dmitry; Ylijoki, Kai E. O.; Kuendig, E. Peter [Chemical Communications, 2012, vol. 48, # 89, p. 10957 - 10959]
[10]Katayev, Dmitry; Jia, Yi-Xia; Sharma, Akhilesh K.; Banerjee, Dipshikha; Besnard, Celine; Sunoj, Raghavan B.; Kuendig, E. Peter [Chemistry - A European Journal, 2013, vol. 19, # 36, p. 11916 - 11927]
[11]Zhang, Peng; Zeng, Jia; Pan, Ping; Zhang, Xue-Jing; Yan, Ming [Organic Letters, 2022, vol. 24, # 2, p. 536 - 541]

5
[ 5020-21-3 ]
[ 14381-42-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With hydrogen In acetic acid for 12h;
	With hydrogen In ethanol

Reference： [1]Kawasaki, Takayasu; Horimai, Emiko; Ohta, Hiromichi [Bulletin of the Chemical Society of Japan, 1996, vol. 69, # 12, p. 3591 - 3594]
[2]Fisnerova,L. et al. [Collection of Czechoslovak Chemical Communications, 1967, vol. 32, p. 4082 - 4098]

6
[ 14381-42-1 ]
[ 1196-17-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h;	2-1 <2-1> Preparation of indan-1-yl-methanol <2-1> Preparation of indan-1-yl-methanol 150 mg (0.92 mmol) of indan-1-carboxylic acid compound was dissolved in 9 mL of tetrahydrofuran, and then 105 mg (2.77 mmol) of lithium aluminum hydride was added at 0° C. and stirred at room temperature for 2 hours. Water was slowly added to quench the reaction, and when a gel was formed by adding ethyl acetate, the celite was filtered. Then, the residue was dissolved again in 20 mL of ethyl acetate and the organic layer was washed with distilled water three times. The organic layer was dried with anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure to give 124 mg of colorless oil (yield: 91%). 1H-NMR (300 MHz, CDCl3) δ 1.89-2.00 (m, 1H), 2.21-2.33 (m, 1H), 2.83-3.01 (m, 2H), 3.34-3.39 (m, 1H), 3.76-3.82 (m, 2H), 7.15-7.30 (m, 4H)
91%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h;	2-1 Preparation of indan-1-yl-methanol Preparation of indan-1-yl-methanol [0055] tetrahydrofuran, and then 105 mg (2.77 mmol) of lithium aluminum hydride was added at 0 °C and stirred at room temperature for 2 hours. Water was slowly added to quench the reaction, and when a gel was formed by adding ethyl acetate, the celite was filtered. Then, the residue was dissolved again in 20 mL of ethyl acetate and the organic layer was washed with distilled water three times. The organic layer was dried with anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure to give 124 mg of colorless oil (yield: 91%). [0057] 1H-NMR(300 MHz, CDCl3) δ 1.89-2.00(m, 1H), 2.21-2.33(m, 1H), 2.83-3.01 (m, 2H), 3.34-3.39(m, 1 H), 3.76-3.82(m, 2H), 7.15-7.30(m, 4H)MS (m/e, M+): 148
	With lithium aluminium tetrahydride

	With lithium aluminium tetrahydride
	With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 10 - 20℃; for 1.5h;	1 EXAMPLE 1; 1-Indanylmethanol, 1a To a suspension of LiAlH4 (4.7 g) in diethyl ether (200 ml) was added dropwise a solution of AlCl3 in diethyl ether (200 ml). A solution of 1-indanecarboxylic acid (10 g) (prepared according to the method of Hansen et al. Helv. Chim. Acta 1982, 33, 325-343) in dry tetrahydrofuran (200 ml) was added drop-wise at 10-15° C. The mixture was finally stirred at room temperature for 1.5 hours. Excess AlH3 was destroyed by addition of concentrated aqueous NaOH solution (25 ml) at 0° C. Precipitated inorganic salts were filtered off and the solvents evaporated in vacuo leaving 6.8 g of the title compound 1a as a viscous oil which was used without further purification.
	Stage #1: Indan-1-carboxylic acid With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 0.5h; Cooling with ice; Stage #2: With water In tetrahydrofuran Cooling with ice;	6.1 Synthesis of 2,3-dihydro-1H-inden-1-methanol To a solution of 2,3-dihydro-1H-inden-1-carboxylic acid (0.50 g) in tetrahydrofuran (5.0 mL), lithium aluminum hydride (0.18 g) was added under ice-cooling and the resultant reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture, water was added under ice-cooling and the resultant reaction mixture was extracted with ethyl acetate. The organic phase was washed with a saturated saline and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluate: n-hexane:ethyl acetate=85:15 to 75:25) to obtain the subject compound (445 mg) as a colorless oil.

Reference： [1]Current Patent Assignee: ASAN FOUNDATION - US2013/11417, 2013, A1 Location in patent: Paragraph 0088; 0089; 0090; 0091
[2]Current Patent Assignee: ASAN FOUNDATION - EP2562156, 2013, A2 Location in patent: Paragraph 0055; 0056; 0057; 0058
[3]Brewster,J.H.; Buta,J.G. [Journal of the American Chemical Society, 1966, vol. 88, # 10, p. 2233 - 2240] Franz,J.A.; Barrows,R.D.; Camaioni,D.M. [Journal of the American Chemical Society, 1984, vol. 106, p. 3964]
[4]Ranade, Vidyadhar S.; Consiglio, Giambattista; Prins, Roel [Journal of Organic Chemistry, 1999, vol. 64, # 24, p. 8862 - 8867]
[5]Current Patent Assignee: H. LUNDBECK A/S - US6352988, 2002, B2 Location in patent: Page column 16-17
[6]Current Patent Assignee: MOCHIDA PHARMACEUTICAL CO LTD - US2012/220772, 2012, A1 Location in patent: Page/Page column 57-58

7
[ 14381-42-1 ]
[ 121692-26-0 ]

Yield	Reaction Conditions	Operation in experiment
48%	With sulfur tetrafluoride In hexane at 70 - 75℃; for 6h;

Reference： [1]Lorentzen, Ronald J.; Brewster, James H.; Smith, Howard E. [Journal of the American Chemical Society, 1992, vol. 114, # 6, p. 2181 - 2187]

8
[ 124-38-9 ]
3-1H-indenyllithium [ No CAS ]
[ 14381-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen 2.) THF, acetic acid, 25 deg C; Yield given. Multistep reaction;

Reference： [1]Franz,J.A.; Barrows,R.D.; Camaioni,D.M. [Journal of the American Chemical Society, 1984, vol. 106, p. 3964]

9
[ 26452-96-0 ]
[ 14381-42-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydroxide for 2h; Heating;

Reference： [1]Nongrum, F.M.; Myrboh, B. [Synthesis, 1987, # 9, p. 845 - 846]

10
[ 124-38-9 ]
[ 95-13-6 ]
[ 14381-42-1 ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: 1-indene With 9-borabicyclo[3.3.1]nonane dimer In 1,2-dimethoxyethane at 70℃; for 24h; Glovebox; Stage #2: carbon dioxide With cesium fluoride In 1,2-dimethoxyethane at 120℃; for 24h; Glovebox; regioselective reaction;
	With hydrogen Multistep reaction;

Reference： [1]Gevorgyan, Ashot; Obst, Marc F.; Guttormsen, Yngve; Maseras, Feliu; Hopmann, Kathrin H.; Bayer, Annette [Chemical Science, 2019, vol. 10, # 43, p. 10072 - 10078]
[2]Iriuchijima, Shinobu; Keiyu, Atsuko [Agricultural and Biological Chemistry, 1981, vol. 45, # 6, p. 1389 - 1392]

11
Sodium; 1H-indene-1-carboxylate [ No CAS ]
[ 14381-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; nickel

Reference： [1]Brewster,J.H.; Buta,J.G. [Journal of the American Chemical Society, 1966, vol. 88, # 10, p. 2233 - 2240]

12
[ 14381-42-1 ]
[ 33695-57-7 ]

Yield	Reaction Conditions	Operation in experiment
	(i) SOCl₂, benzene, (ii) aq. NH₃; Multistep reaction;
	Multi-step reaction with 2 steps 1: thionyl chloride / 0.33 h / 40 °C 2: NH₃ / tetrahydrofuran / 0.5 h / 20 °C
	Multi-step reaction with 2 steps 1: thionyl chloride / 2 h / Thermolysis 2: aq. NH₃ / 24 h / 20 °C

Multi-step reaction with 2 steps 1: SOCl₂ 2: NH₃

Reference： [1]Seidl,G. et al. [Tetrahedron, 1964, vol. 20, p. 633 - 640]
[2]Ranade, Vidyadhar S.; Consiglio, Giambattista; Prins, Roel [Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1132 - 1138]
[3]Ranade, Vidyadhar S.; Consiglio, Giambattista; Prins, Roel [Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1132 - 1138]
[4]Ray; Lahiri [Journal of the Indian Chemical Society, 1990, vol. 67, # 4, p. 324 - 326]

13
[ 29427-69-8 ]
[ 14381-42-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen In methanol at 20℃; for 18h;	124.124a Example 124; N-(4-(3-(((3-chloro-4-(methyloxy)phenyl)amino)carbonyl)phenyl)-1,3-thiazol-2-yl)-2,3-dihydro-1H-indene-1-carboxamide; (124a) A MeOH (1 mL) solution of 3-oxo-indancarboxylic acid (85.5 mg, 0.485 mmol) was mixed with Pd/C (16.5 mg) and hydrogenated at room temperature under 55 psi H2 pressure for 18 h. The crude mixture was filtered and concentrated to give 1-indanecarboxylic acid (74.4 mg, 95%). MS Found: (M-H)-=161.
93%	With hydrogenchloride; mercury dichloride; zinc In toluene for 12h; Heating;
88%	With palladium 10% on activated carbon; hydrogen In methanol at 20℃;	7.iii Step (iii): N-(6-(3-(Dimethylamino)-l-phenylpropoxy)pyridin-3-yl)-2,3-dihydro -lH-indene-1-carboxamide (AG-0173) . Replacement of the urea oxygen by sulphur was easily achieved by reaction of e.g., amine B6 with thiophosgene and quenching of the intermediate isothiocyanate with indole. Secondly, the indane-l -carboxamide C2 in which the indole nitrogen is replaced by methylene, was obtained by coupling of e.g., an indane using EDCI/HOBt (see Scheme CI). N-aryl urea C3 was obtained by alkylation of compound B3. For R2 = Boc and Ri, R2 = Phth the corresponding secondary and primairy amines were obtained by e.g., HC1 (R2 = Boc) and N2H4 (Ri, R2 = Phth).3-Oxo-2,3-dihydro-lH-indene-l-carboxylic acid (100 mg, 0.57 mmol, 1.0 eq) was dissolved in methanol. A spatula tip of Pd/C (10%) was added and the mixture was stirred under 5 bar hydrogen overnight at rt. The mixture was filtered over Celite and the pad washed with methanol. The filtrate was concentrated to yield 2,3-dihydro-lH- indene-l-carboxylic acid as a colorless oil (81 mg, 0,46 mmol, 88%).

	With hydrogen
	With hydrogen In ethanol for 24h;
	With hydrogen In ethanol

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2007/185056, 2007, A1 Location in patent: Page/Page column 51
[2]Mermerian, Ara H.; Fu, Gregory C. [Journal of the American Chemical Society, 2005, vol. 127, # 15, p. 5604 - 5607]
[3]Current Patent Assignee: AAPA - WO2014/46544, 2014, A1 Location in patent: Page/Page column 18; 32
[4]Ranade, Vidyadhar S.; Consiglio, Giambattista; Prins, Roel [Journal of Organic Chemistry, 1999, vol. 64, # 24, p. 8862 - 8867]
[5]Katz, Christopher E.; Aube, Jeffrey [Journal of the American Chemical Society, 2003, vol. 125, # 46, p. 13948 - 13949]
[6]Ranade, Vidyadhar S.; Consiglio, Giambattista; Prins, Roel [Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1132 - 1138]

14
[ 14381-42-1 ]
perhydroindan-1-carboxylic acid [ No CAS ]
(1R,3aR,7aR)-Octahydro-indene-1-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In ethanol at 20℃;
	With hydrogen In ethanol at 20℃; Title compound not separated from byproducts.;

Reference： [1]Ranade, Vidyadhar S.; Consiglio, Giambattista; Prins, Roel [Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1132 - 1138]
[2]Ranade, Vidyadhar S.; Consiglio, Giambattista; Prins, Roel [Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1132 - 1138]

15
[ 14209-41-7 ]
sodium amalgam [ No CAS ]
[ 14381-42-1 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1920,vol. 170,p. 467
Bulletin de la Societe Chimique de France,1920,vol. <4> 27,p. 789

16
[ 14381-42-1 ]
[ 67-63-0 ]
[ 214461-31-1 ]

Yield	Reaction Conditions	Operation in experiment
71%	for 12h; Heating;

Reference： [1]Mermerian, Ara H.; Fu, Gregory C. [Journal of the American Chemical Society, 2005, vol. 127, # 15, p. 5604 - 5607]

17
[ 14381-42-1 ]
[ 848170-27-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ / Heating 2: pyridine / 0 - 20 °C

Reference： [1]Daum, Sebastian; Erdmann, Frank; Fischer, Gunter; De Lacroix, Boris Feaux; Hessamian-Alinejad, Anahita; Houben, Sabine; Frank, Walter; Braun, Manfred [Angewandte Chemie - International Edition, 2006, vol. 45, # 44, p. 7454 - 7458]

18
[ 14381-42-1 ]
[ 920508-13-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: SOCl₂ / Heating 2.1: pyridine / 0 - 20 °C 3.1: nBuLi / diethyl ether / -78 °C 3.2: diethyl ether

Reference： [1]Daum, Sebastian; Erdmann, Frank; Fischer, Gunter; De Lacroix, Boris Feaux; Hessamian-Alinejad, Anahita; Houben, Sabine; Frank, Walter; Braun, Manfred [Angewandte Chemie - International Edition, 2006, vol. 45, # 44, p. 7454 - 7458]

19
[ 14381-42-1 ]
(2-hydroxy-phenyl)-indan-1-yl-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: SOCl₂ / Heating 2.1: pyridine / 0 - 20 °C 3.1: nBuLi / diethyl ether / -78 °C 3.2: diethyl ether 4.1: AlCl₃ / CH₂Cl₂ / 0 °C

Reference： [1]Daum, Sebastian; Erdmann, Frank; Fischer, Gunter; De Lacroix, Boris Feaux; Hessamian-Alinejad, Anahita; Houben, Sabine; Frank, Walter; Braun, Manfred [Angewandte Chemie - International Edition, 2006, vol. 45, # 44, p. 7454 - 7458]

20
[ 14381-42-1 ]
[ 920508-14-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: SOCl₂ / Heating 2.1: pyridine / 0 - 20 °C 3.1: nBuLi / diethyl ether / -78 °C 3.2: diethyl ether

Reference： [1]Daum, Sebastian; Erdmann, Frank; Fischer, Gunter; De Lacroix, Boris Feaux; Hessamian-Alinejad, Anahita; Houben, Sabine; Frank, Walter; Braun, Manfred [Angewandte Chemie - International Edition, 2006, vol. 45, # 44, p. 7454 - 7458]

21
[ 14381-42-1 ]
(5-fluoro-2-hydroxy-phenyl)-indan-1-yl-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: SOCl₂ / Heating 2.1: pyridine / 0 - 20 °C 3.1: nBuLi / diethyl ether / -78 °C 3.2: diethyl ether 4.1: AlCl₃ / CH₂Cl₂ / 0 °C

Reference： [1]Daum, Sebastian; Erdmann, Frank; Fischer, Gunter; De Lacroix, Boris Feaux; Hessamian-Alinejad, Anahita; Houben, Sabine; Frank, Walter; Braun, Manfred [Angewandte Chemie - International Edition, 2006, vol. 45, # 44, p. 7454 - 7458]

22
[ 14381-42-1 ]
(5-fluoro-2-methoxy-phenyl)-(1-methyl-indan-1-yl)-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: SOCl₂ / Heating 2.1: pyridine / 0 - 20 °C 3.1: nBuLi / diethyl ether / -78 °C 3.2: diethyl ether 4.1: LDA / tetrahydrofuran / -78 - 0 °C 4.2: tetrahydrofuran / -20 - 20 °C

Reference： [1]Daum, Sebastian; Erdmann, Frank; Fischer, Gunter; De Lacroix, Boris Feaux; Hessamian-Alinejad, Anahita; Houben, Sabine; Frank, Walter; Braun, Manfred [Angewandte Chemie - International Edition, 2006, vol. 45, # 44, p. 7454 - 7458]

23
[ 14381-42-1 ]
[ 851166-12-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 71 percent / sulfuric acid; MgSO₄ / 12 h / Heating 2.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C 2.2: 80 percent / tetrahydrofuran; hexane / -78 - 20 °C

Reference： [1]Mermerian, Ara H.; Fu, Gregory C. [Journal of the American Chemical Society, 2005, vol. 127, # 15, p. 5604 - 5607]

24
[ 14381-42-1 ]
1-acetyl-indan-1-carboxylic acid isopropyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 71 percent / sulfuric acid; MgSO₄ / 12 h / Heating 2.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C 2.2: 80 percent / tetrahydrofuran; hexane / -78 - 20 °C 3.1: chiral-plannar ferrocenyl derivative / CH₂Cl₂ / 24 h / 20 °C

Reference： [1]Mermerian, Ara H.; Fu, Gregory C. [Journal of the American Chemical Society, 2005, vol. 127, # 15, p. 5604 - 5607]

25
[ 14381-42-1 ]
[ 26452-96-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With methanol; sulfuric acid Reflux;
	Multi-step reaction with 2 steps 1: SOCl₂ / CH₂Cl₂ / 0.75 h 2: 2.05 g / CH₂Cl₂ / 3 h

Reference： [1]Location in patent: experimental part Pietruszka, Joerg; Simon, Robert Christian; Kruska, Fabian; Braun, Manfred [European Journal of Organic Chemistry, 2009, # 35, p. 6217 - 6224]
[2]Katz, Christopher E.; Aube, Jeffrey [Journal of the American Chemical Society, 2003, vol. 125, # 46, p. 13948 - 13949]

26
[ 14381-42-1 ]
[ 57021-68-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: SOCl₂ / CH₂Cl₂ / 0.75 h 2.1: 2.05 g / CH₂Cl₂ / 3 h 3.1: LDA / tetrahydrofuran / 1 h / -78 °C 3.2: 58 percent / tetrahydrofuran / -78 - 20 °C 4.1: 70 percent / LAH / diethyl ether / 18 h / 20 °C
	Multi-step reaction with 3 steps 1.1: thionyl chloride / dichloromethane / 1 h / 20 - 30 °C 1.2: 3 h / 20 - 30 °C 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: -78 - 30 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 30 °C
	Multi-step reaction with 3 steps 1.1: thionyl chloride / dichloromethane / 1 h / 20 °C 1.2: 3 h / 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C

Reference： [1]Katz, Christopher E.; Aube, Jeffrey [Journal of the American Chemical Society, 2003, vol. 125, # 46, p. 13948 - 13949]
[2]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - WO2020/47082, 2020, A1
[3]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - WO2020/205538, 2020, A1

27
[ 14381-42-1 ]
[ 637356-69-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: SOCl₂ / CH₂Cl₂ / 0.75 h 2.1: 2.05 g / CH₂Cl₂ / 3 h 3.1: LDA / tetrahydrofuran / 1 h / -78 °C 3.2: 58 percent / tetrahydrofuran / -78 - 20 °C 4.1: 70 percent / LAH / diethyl ether / 18 h / 20 °C 5.1: 51 percent / hydrazoic acid; PPh₃; DEAD / tetrahydrofuran; benzene / 18 h / 20 °C

Reference： [1]Katz, Christopher E.; Aube, Jeffrey [Journal of the American Chemical Society, 2003, vol. 125, # 46, p. 13948 - 13949]

28
[ 14381-42-1 ]
[ 637356-93-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: SOCl₂ / CH₂Cl₂ / 0.75 h 2.1: 2.05 g / CH₂Cl₂ / 3 h 3.1: LDA / tetrahydrofuran / 1 h / -78 °C 3.2: 58 percent / tetrahydrofuran / -78 - 20 °C
	Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / 1 h / 20 - 30 °C 1.2: 3 h / 20 - 30 °C 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: -78 - 30 °C
	Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / 1 h / 20 °C 1.2: 3 h / 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 20 °C

Reference： [1]Katz, Christopher E.; Aube, Jeffrey [Journal of the American Chemical Society, 2003, vol. 125, # 46, p. 13948 - 13949]
[2]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - WO2020/47082, 2020, A1
[3]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - WO2020/205538, 2020, A1

29
[ 14381-42-1 ]
1-(1'-hydroxymethyl-indan-1'-ylmethyl)-5-tert-butyl-azepan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: SOCl₂ / CH₂Cl₂ / 0.75 h 2.1: 2.05 g / CH₂Cl₂ / 3 h 3.1: LDA / tetrahydrofuran / 1 h / -78 °C 3.2: 58 percent / tetrahydrofuran / -78 - 20 °C 4.1: 70 percent / LAH / diethyl ether / 18 h / 20 °C 5.1: 51 percent / hydrazoic acid; PPh₃; DEAD / tetrahydrofuran; benzene / 18 h / 20 °C 6.1: BF₃*OEt₂ / CH₂Cl₂ / 24 h / -78 - 20 °C 6.2: aq. KOH / CH₂Cl₂ / 0.5 h / 20 °C

Reference： [1]Katz, Christopher E.; Aube, Jeffrey [Journal of the American Chemical Society, 2003, vol. 125, # 46, p. 13948 - 13949]

30
[ 95-13-6 ]
[ 14381-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) BuLi / 1.) hexane, ether, room temperature, 10 min, 2.) -78 deg C, 15 min 2: 82 percent / H₂ / Pd-C / acetic acid / 12 h

Reference： [1]Kawasaki, Takayasu; Horimai, Emiko; Ohta, Hiromichi [Bulletin of the Chemical Society of Japan, 1996, vol. 69, # 12, p. 3591 - 3594]

31
[ 14381-42-1 ]
1-(2,3-dihydro-1,4-benzodioxin-5-yl)-4-(indan-1-yl-methyl)piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) carbonyldiimidazole / 1.) CH₂Cl₂, 2 h, 2.) CH₂Cl₂, RT, overnight 2: LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

Reference： [1]Peglion; Canton; Bervoets; Audinot; Brocco; Gobert; Le Marouille-Girardon; Millan [Journal of Medicinal Chemistry, 1995, vol. 38, # 20, p. 4044 - 4055]

32
[ 14381-42-1 ]
[ 111140-68-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 78 percent / SOCl₂ / CH₂Cl₂ / 5 h / Heating 2: dimethylformamide / 12 h / 30 °C

Reference： [1]Sarges; Schnur; Belletire; Peterson [Journal of Medicinal Chemistry, 1988, vol. 31, # 1, p. 230 - 243]

33
[ 14381-42-1 ]
[ 90320-62-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: LiAlH₄ 2: 72 percent / triphenylphosphine, Cl₂ / dimethylformamide / -10 °C

Reference： [1]Franz,J.A.; Barrows,R.D.; Camaioni,D.M. [Journal of the American Chemical Society, 1984, vol. 106, p. 3964]

34
[ 14381-42-1 ]
[ 123883-00-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: oxalyl chloride / CH₂Cl₂ / 1.) room temp., 1 h, 2.) reflux, 1 h 2: CH₂Cl₂ / 16 h