[ CAS No. 21737-58-6 ] {[proInfo.proName]}

Name: 21737-58-6|5H-Dibenzo[b,f]azepin-10(11H)-one|98%
Brand: Ambeed
SKU: A338333
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Quality Control of [ 21737-58-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 21737-58-6 ]

Product Details of [ 21737-58-6 ]

CAS No. :	21737-58-6	MDL No. :	MFCD00101078
Formula :	C₁₄H₁₁NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VSZGCLXGCOECAY-UHFFFAOYSA-N
M.W :	209.24	Pubchem ID :	11160106
Synonyms :		Chemical Name :	5H-Dibenzo[b,f]azepin-10(11H)-one

Calculated chemistry of [ 21737-58-6 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.07
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	67.16
TPSA :	29.1 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.03
Log Po/w (XLOGP3) :	2.91
Log Po/w (WLOGP) :	2.79
Log Po/w (MLOGP) :	2.48
Log Po/w (SILICOS-IT) :	3.19
Consensus Log Po/w :	2.68

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.53
Solubility :	0.0624 mg/ml ; 0.000298 mol/l
Class :	Soluble
Log S (Ali) :	-3.18
Solubility :	0.138 mg/ml ; 0.000658 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.41
Solubility :	0.00081 mg/ml ; 0.00000387 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.47

Safety of [ 21737-58-6 ]

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

Application In Synthesis of [ 21737-58-6 ]

* 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 [ 21737-58-6 ]
Downstream synthetic route of [ 21737-58-6 ]

[ 21737-58-6 ] Synthesis Path-Upstream 1~4

1
[ 21737-58-6 ]
[ 494-19-9 ]

Reference： [1] Australian Journal of Chemistry, 2013, vol. 66, # 6, p. 635 - 645

2
[ 21737-58-6 ]
[ 256-96-2 ]

Reference： [1] Tetrahedron Letters, 2013, vol. 54, # 22, p. 2841 - 2844

3
[ 21737-58-6 ]
[ 4014-77-1 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium tetrahydroborate In methanol; water at 45℃; for 1 h;	5H-dibenzo[b,f]azepin-10(11H)-one 6 (350.0 g, 1.67 mol) was suspended in a mixture of water (0.7 L) and methanol (2.8 L), sodium borohydride (76 g, 2.0 mol) was added in portions over 10 min without cooling, and stirring continued at 45 °C for 1 h. Acetone (350 mL) was added cautiously, and the reaction mixture was evaporated down to a small volume. Addition of water (700 mL) precipitated the product (315 g, 89percent) and dried at 60-65˚C to give the (S)-10,11-dihydro-5H-dibenzo[b,f]azepin-10-ol 7b as an off-white solid (315 g) in 89.0percent yield and >98percent purity

Reference： [1] Tetrahedron Letters, 2013, vol. 54, # 22, p. 2841 - 2844

4
[ 21737-58-6 ]
[ 29331-92-8 ]

Reference： [1] Patent: US2016/122332, 2016, A1,

[ 21737-58-6 ] Synthesis Path-Downstream 1~80

Yield	Reaction Conditions	Operation in experiment
		4) Potassium tert-butoxide (3.1 g) and water (153 mul) were added to a tetrahydrofuran (20 ml) solution of the compound (1.01 g) obtained in 3), and the solution was stirred at 80 C. for 1.5 hours under heating. The solution was allowed to cool and poured into water, followed by extraction with ethyl acetate. The organic phase was washed with water and saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and the resulting residue was purified by silica gel column chromatography (developing solvent, ethyl acetate: hexane=1:5) to obtain 10,11-dihydro-10-oxo-5H-dibenzo[b,f]azepine (624 mg; yield, 69%) as a yellow solid.

2
[ 1189-71-5 ]
[ 21737-58-6 ]
[ 28721-07-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	In dichloromethane; at 0 - 5℃;Inert atmosphere;	To a solution of azepine-10-One (25 g, 0.119 mol) in Dichloromethane (200 ml) was dropwise added the solution of chloro sulphonyl isocyanate (32.6g, 0.230 mol) in Dichloromethane (100 ml) under nitrogen atmosphere at 0-5 C. After the addition of chloro sulphonyl isocyanate, reaction mixture was stirred for 1-2 hrs at 0-5 C. The Progress of reaction was monitored by TLC. Reaction mixture was quenched with Glacial acetic acid (25 ml) followed by addition of DM water (150 ml) at 10-15 C. Layers were separated and Aq. layer was re-extracted with Dichloromethane (3*200 ml). Combined Dichloromethane layer was distilled off at reduced pressure at 40-45 C. Product was further crystallized with Isopropyl alcohol (100 ml) to get pure azepine amide (27.90 g, 93%) with 98.52% Purity by HPLC.

Reference： [1]Patent: US2016/122332,2016,A1 .Location in patent: Paragraph 0135-0136
[2]Tetrahedron Letters,2001,vol. 42,p. 385 - 389
[3]Tetrahedron Letters,2004,vol. 45,p. 5275 - 5278
[4]Organic Letters,2005,vol. 7,p. 4787 - 4789

3
[ 10464-31-0 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 385 - 389

4
[ 332081-70-6 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 385 - 389

5
[ 332081-68-2 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 385 - 389

6
[ 353497-31-1 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5275 - 5278
[2]Organic Process Research and Development,2005,vol. 9,p. 272 - 277

7
[ 731851-85-7 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5275 - 5278

8
[ 869668-73-5 ]
[ 21737-58-6 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 4787 - 4789
[2]Tetrahedron,2007,vol. 63,p. 690 - 702
[3]RSC Advances,2015,vol. 5,p. 20516 - 20520

9
[ 869668-71-3 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 690 - 702
[2]Organic Letters,2005,vol. 7,p. 4787 - 4789

10
[ 1859-70-7 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 690 - 702
[2]Organic Letters,2005,vol. 7,p. 4787 - 4789

11
[ 551-93-9 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 690 - 702
[2]Organic Letters,2005,vol. 7,p. 4787 - 4789

12
[ 3335-98-6 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5275 - 5278
[2]Organic Process Research and Development,2005,vol. 9,p. 272 - 277
[3]Organic Process Research and Development,2005,vol. 9,p. 272 - 277
[4]Organic Process Research and Development,2005,vol. 9,p. 272 - 277

13
[ 39507-06-7 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5275 - 5278
[2]Tetrahedron Letters,2004,vol. 45,p. 5275 - 5278
[3]Organic Process Research and Development,2005,vol. 9,p. 272 - 277

14
[ 805236-74-2 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5275 - 5278
[2]Tetrahedron Letters,2004,vol. 45,p. 5275 - 5278
[3]Organic Process Research and Development,2005,vol. 9,p. 272 - 277

15
[ 353497-35-5 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5275 - 5278
[2]Tetrahedron Letters,2004,vol. 45,p. 5275 - 5278
[3]Organic Process Research and Development,2005,vol. 9,p. 272 - 277

16
[ 731851-92-6 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5275 - 5278

17
[ 731851-81-3 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5275 - 5278

18
{2-[Phenyl-(2,2,2-trifluoro-acetyl)-amino]-phenyl}-acetic acid benzyl ester [ No CAS ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5275 - 5278

19
sodium; (2-phenylamino-phenyl)-acetate [ No CAS ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5275 - 5278

20
[ 54616-47-6 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 385 - 389

21
[ 76041-86-6 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 385 - 389
[2]Tetrahedron Letters,2001,vol. 42,p. 385 - 389
[3]Tetrahedron Letters,2001,vol. 42,p. 385 - 389

22
[ 95-53-4 ]
<carbo-p-cresyloxy->-thiocarbamide [ No CAS ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 385 - 389
[2]Tetrahedron Letters,2001,vol. 42,p. 385 - 389
[3]Tetrahedron Letters,2001,vol. 42,p. 385 - 389
[4]Tetrahedron Letters,2001,vol. 42,p. 385 - 389

23
[ 353497-28-6 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 385 - 389

24
[ 1027035-99-9 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 385 - 389
[2]Tetrahedron Letters,2001,vol. 42,p. 385 - 389
[3]Tetrahedron Letters,2001,vol. 42,p. 385 - 389

25
[ 332081-66-0 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 385 - 389

26
[ 332081-67-1 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 385 - 389

27
[ 332081-60-4 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 385 - 389

28
[ 332081-64-8 ]
[ 21737-58-6 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 385 - 389

29
[ 1189-71-5 ]
[ 21737-58-6 ]
C₁₆H₁₃ClN₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	In dichloromethane; at 0 - 10℃;	EXAMPLE 2; Preparation of 10-Oxo-10,11-dihydro-5H-dibenz[b,f]azepin-5-carboxamide III; A 1-L, three-necked flask equipped with a thermometer, nitrogen inlet, mechanical stirrer and addition funnel, was charged with oximinostilbene IV (prepared above) followed by 400 mL dichloromethane. The suspension was cooled to 0-5 C. and a solution of chlorosulfonyl isocyanate (71.7 g, 0.50 mol) in 200 mL dichloromethane was added dropwise, maintaining the internal temperature at 0-10 C. Following the addition, the reaction mixture was maintained at 0-5 C. until reaction completion. The cold suspension was then filtered and washed giving oxcarbazepine intermediate V (163 g, 97%). The damp solid was suspended in 300 ml glacial acetic acid and cooled to 10-15 C. To the suspension was added 188 mL cold water, portionwise, maintaining the IT<20 C. The mixture was maintained at 15-25 C. for 0.5-1.0 h until reaction completion. The suspension was concentrated to 200-300 ml and 700 mL isopropanol was added to precipitate the product. The suspension was then filtered and washed. The damp cake was purified in an isopropanol:water mixture to furnish oxcarbazepine as a white to off-white solid (101.27 g, 84%, purity of 99.5% by HPLC). 1H NMR (DMSO, d): 4.06, 6.19, 7.30-7.39, 7.44-7.51, 7.63, 7.91 ppm.

Reference： [1]Patent: US2005/282797,2005,A1 .Location in patent: Page/Page column 3

30
[ 4698-11-7 ]
[ 21737-58-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogenchloride; water; In acetone; at 20℃; for 1 - 1.5h;	EXAMPLE I; Preparation of 5,11-Dihydro-10H-dibenz[b,f]azepine-10-one (Oximinostilbene) IV; A 2-L, three-necked flask equipped with a mechanical stirrer, thermometer and nitrogen inlet was charged with 10-methoxyiminostilbene I (110.0 g, 0.49 mol) and 330 mL acetone. A 10% solution of hydrochloric acid (28.6 g, 0.08 mol) was then added. The reaction mixture was stirred at ambient temperature for 1-1.5 hours until reaction completion. The product was precipitated by the addition of 660 mL of deionized water, and the resulting suspension was stirred for 3-4 hours. The suspension was filtered and washed with water. After drying, oximinostilbene (99.92 g, 97%) was obtained as a bright yellow solid having a purity of 99% by HPLC. 1H NMR (CDCl3, d): 3.80, 6.87, 7.04-7.15, 7.22-7.24, 7.32-7.37, 8.04 ppm.
85.4%	With hydrogenchloride; In water; isopropyl alcohol; at 25 - 65℃;	10-Methoxy-5H-dibenzo[b,f]azepine 4 (500 g, 2.23 mol) and isopropanol (1.0 L) were charged into a round bottomed flask and stirred for 5-10 min. 50% Aqueous hydrochloride solution (250 mL) was then added slowly to the mixture at 25-35 ?C and stirred for 15 min. The reaction mixture was heated to 60-65 ?C and maintained for 2-3 h. The progress of the reaction was monitored by TLC, and after completion of the reaction (by TLC), ethyl acetate (1.5 L) and water (1.0 L) were added into the reaction mixture and stirred for 5-10 min. Organic layer was separated and the aqueous layer was extracted with ethyl acetate (1.5 L). The combined organic layer was washed with 5% caustic lye solution (500 mL) followed by 10 % NaCl solution (500 mL) and evaporated at 50-55?C under reduced pressure. n-Hexane (500 mL) was then added into the crude product at 25-30 ?C and stirred for 1-2 h. The obtained solid was collected by filtration, washed with n-hexane (250 mL) and dried at 60-65 ?C to afford the title compound 6 as yellow solid (400 g) in 85.4% yield and >98.2% purity. Spectroscopic data were found to be in agreement with the data collected from authentic sample of intermediate 6. IR (KBR): 3329, 3284, 3040, 1643, 1474, 1309, 753 cm-1; 1H NMR (400 MHz, CDCl3): delta 3.72 (2H, s), 6.78-7.91 (8H, m); 13C NMR (400 MHz, CDCl3): delta 49.4, 119.1, 119.2, 119.8, 124.1, 124.5, 127.7, 127.9, 129.8, 130.3, 133.7, 141.5, 146.8, 190.1; HRMS calcd for C14H11NO, 210.0919; found 210.0909.

Reference： [1]Organic Process Research and Development,2005,vol. 9,p. 272 - 277
[2]Patent: US2005/282797,2005,A1 .Location in patent: Page/Page column 3
[3]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4319 - 4324
[4]Tetrahedron Letters,2013,vol. 54,p. 2841 - 2844

31
[ 4698-11-7 ]
[ 7440-44-0 ]
[ 21737-58-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethanol; toluene;	EXAMPLE 11 10-oxo-10,11-dihydro-5H-dibenz(b,f)azepine 22.3 g of 10-methoxy-5H-dibenz(b,f)azepine are heated under reflux with 100 ml of 2N hydrochloric acid for 2 hours. The gummy residue is extracted with chloroform (50÷50 ml), the combined extracts are washed with water and evaporated to dryness under vacuum. The residue is taken up into 200 ml of ethanol, treated with charcoal (2 g) for 1 h under reflux, filtered, evaporated to dryness under vacuum, finally taken up into 50÷50 ml of toluene, stripping thoroughly. The residue is kept for further working-up.

Reference： [1]Patent: US5808058,1998,A

32
[ 28721-07-5 ]
[ 21737-58-6 ]

Reference： [1]Synthetic Communications,2013,vol. 43,p. 1508 - 1516
[2]Organic Process Research and Development,2012,vol. 16,p. 710 - 713

33
[ 21737-58-6 ]
(R)-(-)-10,11-dihydro-5H-dibenzo[b,f]azepin-10-ol [ No CAS ]
((s)-10-hydroxy-10,11-dihydro-5H-dibenzo[b,f]azepin) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [iridium(dihydride)(chloride)((3,5-(tBu)2-C6H3)2P)(C17H10)NHCHC5H3N(CH3)]; hydrogen; potassium carbonate; In butan-1-ol; at 25℃; under 13501.4 - 15001.5 Torr;Autoclave;	Under nitrogen protection,Weigh 1.0mg (0.001mmol) of chiral catalyst C1 (X is 6-methyl),13.8mg (0.1mmol) potassium carbonateAnd 418.6 mg (2 mmol) of <strong>[21737-58-6]5,11-dihydro-10H-dibenzo[b,f]azepin-10-one</strong> into the reaction tube,Add 6mL of n-butanol to the inner tube of the reaction,Put the reaction tube into the autoclave,The gas in the kettle was replaced with hydrogen to maintain the hydrogen pressure at 1.8 to 2.0 MPa, and the reaction was stirred at 25 C until the hydrogen pressure did not decrease and the reaction was stopped.The reaction solution was concentrated. 10 mL of water and 10 mL of ethyl acetate were added to the system, and the layers were separated. The aqueous phase was extracted twice more with ethyl acetate (10 mL x 2), and the organic phases were combined, washed once with saturated brine, and dried over anhydrous sodium sulfate.Suction filtration, spin-drying the solvent to obtain (S)-5,11-dihydro-10H-dibenzo[b,f]azepin-10-ol 266mg, yield 63%According to NMR analysis, the raw material 5,11-dihydro-10H-dibenzo [b, f] aza-10-one has not been completely converted.The product was analyzed by chiral HPLC and its optical purity was 88.1% ee.

Reference： [1]Organic Process Research and Development,2012,vol. 16,p. 710 - 713
[2]Tetrahedron Letters,2013,vol. 54,p. 2841 - 2844
[3]Patent: CN110790708,2020,A .Location in patent: Paragraph 0053-0056; 0063; 0064; 0071; 0072; 0081; 0082

34
[ 21737-58-6 ]
[ 21737-59-7 ]

Reference： [1]Synthetic Communications,2013,vol. 43,p. 1508 - 1516

35
[ 21737-58-6 ]
6, 7-dihydrodibenzo[b,g][1,5]diazocin-5(12H)-one [ No CAS ]

Reference： [1]Synthetic Communications,2013,vol. 43,p. 1508 - 1516

36
[ 21737-58-6 ]
[ 298-46-4 ]

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 2841 - 2844

37
[ 21737-58-6 ]
[ 256-96-2 ]

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 2841 - 2844

38
[ 21737-58-6 ]
((s)-10-hydroxy-10,11-dihydro-5H-dibenzo[b,f]azepin) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With [iridium(dihydride)(chloride)((3,5-(tBu)2-C6H3)2P)(C17H10)NHCHC5H3N(CH3)]; potassium tert-butylate; hydrogen; In butan-1-ol; at 25℃; under 13501.4 - 15001.5 Torr;Autoclave;	Under nitrogen protection,Weigh 1.0mg (0.001mmol) of chiral catalyst C1 (X is 6-methyl),11.2 mg (0.1 mmol) of potassium tert-butoxide and418.6mg (2mmol) of <strong>[21737-58-6]5,11-dihydro-10H-dibenzo[b,f]azepin-10-one</strong> into the inner tube of the reaction,Add 6 mL of n-butanol to the inner tube of the reaction.Put the reaction tube into the autoclave,Replace the gas in the kettle with hydrogen,Keep the hydrogen pressure at 1.8 2.0MPa,The reaction vessel was stirred at 25 C until the hydrogen pressure did not drop any more, and the reaction was stopped.The reaction solution was concentrated.10 mL of water and 10 mL of ethyl acetate were added to the system, and the layers were separated.The aqueous phase was extracted twice more with ethyl acetate (10 mL x 2), and the organic phases were combined.Wash again with saturated saline and dry over anhydrous sodium sulfate.Suction filtration,The solvent was spin-dried to obtain 406 mg of (S)-5,11-dihydro-10H-dibenzo[b,f]azepin-10-ol, with a yield of 96%.According to NMR analysis, the conversion of 5,11-dihydro-10H-dibenzo [b, f] aza-10-one was complete.The product was analyzed by chiral HPLC and its optical purity was 99.2% ee.
91%	With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In dichloromethane; toluene; at -5 - 10℃;	Dichloromethane (1.0 L) and borane dimethyl sulfide (216 mL, 2.17 mol) were charged into a round bottomed flask and stirred for 10 min, and was cooled to -5-0?C. R-2-Me-CBS (methyl oxazaborolidine, 1M in toluene) (335 mL, 0.33 mol) was then added to the reaction flask at -5-0?C and stirred for 10 min. A solution of <strong>[21737-58-6]5H-dibenzo[b,f]azepin-10(11H)-one</strong> 6 (350.0 g, 1.67 mol) in dichloromethane (1.75 L) was added to the reaction mixture. The reaction mixture was warmed to 0-10?C and maintained for 3-4 h at the same temperature. The reaction was monitored by TLC, and after completion of the reaction, methanol (140.0 mL), 5% H2O2 (700 mL) solution and 2N H2SO4 solution (700 mL) were added to the reaction mixture and stirred for 15-20 min. The organic layer was separated and washed with 5 % Na2SO3 solution (875 mL), followed by 10 % NaCl solution (875 mL). The solvent was evaporated at 35-40 ?C under reduced pressure. Water (700.0 mL) was added to the crude product thus obtained at 25-30?C and stirred for 1 h. The product was filtered off, washed with water (350 mL) and dried at 60-65?C to give the (S)(-)-10,11-dihydro-5H-dibenzo[b,f]azepin-10-ol 7a as an off-white solid (321.7 g) in 91% yield and >98.5% purity. Spectroscopic data were found to be in agreement with the data collected from authentic sample of intermediate 7a. 99 % ee. [alpha]D25: -38.5 (c =1, Chloroform); IR (KBR): 3504, 3308, 2937, 1589, 1485, 1331, 762 cm-1; 1H NMR (400 MHz, CDCl3): delta 1.74 (1H, s), 3.09-3.19 (2H, m), 5.02 (1H, m), 6.02 (1H, s), 6.66-7.25 (8H, m); 13C NMR (400 MHz, CDCl3): delta 40.1, 71.7, 117.6, 118.6, 120.1, 121.2, 124.2, 127.6, 128.5, 128.6, 131.5, 131.8, 141.5, 142.9; HRMS calcd for C14H13NO, 212.1075; found 212.1084

Reference： [1]Patent: CN110790708,2020,A .Location in patent: Paragraph 0057-0062; 0065-0070; 0073-0080
[2]Tetrahedron Letters,2013,vol. 54,p. 2841 - 2844

39
[ 21737-58-6 ]
[ 1431547-12-4 ]

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 2841 - 2844
[2]Tetrahedron Letters,2013,vol. 54,p. 2841 - 2844

40
[ 21737-58-6 ]
eslicarbazepine acetate [ No CAS ]

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 2841 - 2844
[2]Tetrahedron Letters,2013,vol. 54,p. 2841 - 2844
[3]Patent: US2016/122332,2016,A1

41
[ 21737-58-6 ]
[ 4014-77-1 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium tetrahydroborate; In methanol; water; at 45℃; for 1h;	<strong>[21737-58-6]5H-dibenzo[b,f]azepin-10(11H)-one</strong> 6 (350.0 g, 1.67 mol) was suspended in a mixture of water (0.7 L) and methanol (2.8 L), sodium borohydride (76 g, 2.0 mol) was added in portions over 10 min without cooling, and stirring continued at 45 C for 1 h. Acetone (350 mL) was added cautiously, and the reaction mixture was evaporated down to a small volume. Addition of water (700 mL) precipitated the product (315 g, 89%) and dried at 60-65?C to give the (S)-10,11-dihydro-5H-dibenzo[b,f]azepin-10-ol 7b as an off-white solid (315 g) in 89.0% yield and >98% purity

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 2841 - 2844

42
[ 23868-11-3 ]
[ 21737-58-6 ]