22651-87-2|Cyclohexanecarboxylic Anhydride| Ambeed

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Quality Control of [ 22651-87-2 ] Purity: 98% SDS Specification

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Product Details of [ 22651-87-2 ]

CAS No. :	22651-87-2
Formula :	C₁₄H₂₂O₃
M.W :	238.32
SMILES Code :	O=C(OC(C1CCCCC1)=O)C2CCCCC2
MDL No. :	MFCD12404944
InChI Key :	JOHUAELJNSBTGS-UHFFFAOYSA-N
Pubchem ID :	89781

Safety of [ 22651-87-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Application In Synthesis of [ 22651-87-2 ]

* 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.

Downstream synthetic route of [ 22651-87-2 ]

[ 22651-87-2 ] Synthesis Path-Downstream 1~36

1
[ 2719-27-9 ]
[ 98-89-5 ]
[ 22651-87-2 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In diethyl ether; for 10h;	To an ether solution (5 mL) of cyclohexanecarboxylic acid (250 mg, 1.95 mmol) was added pyridine (0.5 mL) and cyclohexanecarbonyl chloride (286 mg, 0.261 mL, 1.95 MMOL). After 10 h, the suspension was diluted with ether (20 mL), washed with ice-cold 5% HCl solution (1x50 mL) and concentrated NaHCO3 solution (1x50 mL) and dried over Na2S04. All solvent was removed in vacua to give 350 mg of cyclohexanecarboxylic anhydride as A colorless oil. A portion of the cyclohexanecarboxylic anhydride. (226 mg, 0. 948 mmol) was added to a sodium carbonate solution (1 M, 2 mL) of the aminophosphate 21a (110 mg, 0.412 mmol). After 15 h, it was acidified to PH#1 by addition of concentrated HCI solution at 0 C. Preparative HPLC purification afforded 50 mg (36% yield) of the title compound 25-17. 1H NMR (CD3OD) : δ 7. 27-7. 1 (5H, m), 6.67 (1H, br d), 4.34 (1H, br s), 4.08 (1H, m), 3.96 (1H, m), 2.90 (1H, dd, J=14.4, 6.6 Hz), 2. 78 (1H, dd, J=14.9, 9 Hz), 2.10 (1H, br t), 1.79-1. 51 (5H, m), 1. 33-1. 02 (5H, m); LCMS (ESP): 342 (M+H+) ; 340 (M-H)-.
	With pyridine; In diethyl ether; for 10h;	Example 25-17 Phosphoric acid mono-{2-[(1-cyclohexyl-methanoyl)-amino]-3-phenyl-propyl}ester To an ether solution (5 mL) of cyclohexanecarboxylic acid (250 mg, 1.95 mmol) was added pyridine (0.5 mL) and cyclohexanecarbonyl chloride (286 mg, 0.261 mL, 1.95 mmol). After 10 h, the suspension was diluted with ether (20 mL), washed with ice-cold 5% HCl solution (150 mL) and concentrated NaHCO3 solution (150 mL) and dried over Na2SO4. All solvent was removed in vacuo to give 350 mg of cyclohexanecarboxylic anhydride as a colorless oil.
		General procedure: To a flamed-dried flask with magnetic stir bar, was added aliphatic acid (1.0 equiv), dried DCM (1.0 M) and triethylamine (1.05 equiv) successively. The solution was stirred for 30 minutes at 0 0C. Then acyl chloride (1.05 equiv) was added dropwise to the mixture and stirred overnight at rt. The solvent was evaporated by vacuum to afford the crude mixture. And the mixture was dissolved in n-hexane. Then the residue was filtered through a small plug of celite and concentrated to afford the anhydrides. This product was used to next catalytic reaction without any further purification.

References: [1]New Journal of Chemistry,2019,vol. 43,p. 10711 - 10715.
[2]Organic Letters,2019,vol. 21,p. 7154 - 7157.
[3]Doklady Akademii Nauk SSSR,1936,vol. 13,p. 417.
[4]Patent: WO2004/87720,2004,A1 .Location in patent: Page 57.
[5]Patent: US2005/250742,2005,A1 .Location in patent: Page/Page column 37.
[6]New Journal of Chemistry,2017,vol. 41,p. 931 - 939.
[7]Organic Letters,2019,vol. 21,p. 3625 - 3630.
[8]Tetrahedron,2019,vol. 75,p. 4186 - 4191.

2
[ 98-89-5 ]
[ 22651-87-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With magnesium basic carbonate; di-tert-butyl dicarbonate; at 25℃; for 6h;	Examples 1420 In each example, methacrylic acid anhydride was produced under conditions the same as in Example 1 except that methacrylic acid was replaced with the type of carboxylic acid (6.0 mmol) shown in Table 1, and the amount of magnesium carbonate hydroxide relative to di-t-butyl dicarbonate was changed to 4 mol % or 8 mol %, while the rest of the conditions were set to be the same as in Example 1. The reaction results obtained 412 hours after the start of reactions are shown in Table 1.
90%		General procedure: A few drops of water were added to the mixture of carboxylic acid (1 mmol) and K2CO3 (1.5 mmol, 0.20 g) and put in MW for 2-4 min (900 W), then dry CH3CN (5 mL) and TsCl (0.5 mmol, 0.10 g) were added. The reaction mixture was allowed to ultrasound irradiation for suitable time. After the completion of the reaction, CH2Cl2 or Et2O(2×10 mL) was added to the reaction mixture, stirred, filtered, and the organic layer was dried over CaCl2. The evaporation of the solvent afforded a highly pure product.

References: [1]Heterocycles,2009,vol. 77,p. 629 - 634.
[2]Organic and Biomolecular Chemistry,2012,vol. 10,p. 4509 - 4511.
[3]Patent: US2017/88502,2017,A1 .Location in patent: Paragraph 0076.
[4]Letters in Organic Chemistry,2017,vol. 14,p. 431 - 439.
[5]Journal of Organic Chemistry,1989,vol. 54,p. 1144 - 1149.
[6]Synthesis,2004,p. 205 - 207.
[7]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 3529 - 3530.
[8]European Journal of Organic Chemistry,2019,vol. 2019,p. 5998 - 6002.
[9]Chemistry - A European Journal,2019,vol. 25,p. 2816 - 2823.
[10]Journal of Medicinal Chemistry,2007,vol. 50,p. 828 - 834.
[11]Journal of the American Chemical Society,1951,vol. 73,p. 4275,4278.
[12]Journal of the American Chemical Society,2005,vol. 127,p. 15521 - 15527.
[13]Journal of Medicinal Chemistry,2007,vol. 50,p. 2249 - 2253.
[14]Journal of Organic Chemistry,2015,vol. 80,p. 2874 - 2878.
[15]Patent: DE848355,1943,C .
[16]Organic Letters,2019,vol. 21,p. 3625 - 3630.
[17]Tetrahedron,2019,vol. 75,p. 4186 - 4191.
[18]Chirality,2021,vol. 33,p. 899 - 914.

3
[ 22651-87-2 ]
(+)-N-(2-Phenyl-2-hydroxyethyl)-4-methylthiazolium [ No CAS ]
[ 14272-72-1 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 3666 - 3667.

4
[ 27007-64-3 ]
[ 22651-87-2 ]
2-(3-cyclohexylcarbonyl-2,5-dimethylpyrrol-1-yl)-ethyl methyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55.5%		EXAMPLE 19 Synthesis of 2-(3-cyclohexylcarbonyl-2,5-dimethylpyrrol-1-yl)ethyl methyl ether (234): Compound (234) was prepared in a yield of 55.5% by reacting 2-(2,5-dimethylpyrrol-1-yl)ethyl methyl ether with <strong>[22651-87-2]cyclohexanecarboxylic anhydride</strong> under the same conditions as in Example 16. IR (neat): 2940, 2850, 1740, 1645, 1575, 1520, 1450, 1420, 1395, 1370, 1305, 1290, 1240, 1200, 1170, 1120, 1100, 1030, 1000, 960, 920, 890, 860, 830, 810, 780, 750, 720 cm-1. NMR (CDCl3, δ(ppm)): 1.0-1.9 (10H, m, H on cyclohexane) 2.17 (3H, s, CH3 at the 5-position of the pyrrole ring), 2.50 (3H, s, CH3 at the 2-position of the pyrrole ring), 3.0 (1H, m, --CHCO--), 3.24 (3H, s, OCH3), 3.46 (2H, t, J=5 Hz, --CH2 O--), 3.89 (2H, t, J=5 Hz, --NCH2 --), 6.17 (1H, s, H on the pyrrole ring).

References: [1]Synthetic Communications,1980,vol. 10,p. 773 - 790.
[2]Patent: US4233309,1980,A .

5
[ 111479-66-4 ]
[ 22651-87-2 ]
[ 111479-71-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 623 - 628.

6
[ 38061-25-5 ]
[ 22651-87-2 ]
[ 89205-29-8 ]

References: [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 4417 - 4424.

7
[ 107427-76-9 ]
[ 22651-87-2 ]
[ 111479-84-6 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 623 - 628.

8
[ 22651-87-2 ]
17β-hydroxy-5α-androstanone-(3) [ No CAS ]
[ 20592-38-5 ]

References: [1]Patent: DE661384,1936,C .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 24,p. 495.
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 24,p. 495.
[2]Patent: US2109400,1935,A .

9
[ 22651-87-2 ]
[ 361340-58-1 ]
cyclohexanecarboxylic acid [3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1<i>H</i>-pyrazolo[4,3-<i>d</i>]pyrimidin-5-yl)-4-propoxy-phenyl]-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 1895 - 1899.

10
[ 57605-95-5 ]
[ 22651-87-2 ]
[ 15914-84-8 ]
[ 42177-25-3 ]
Cyclohexanecarboxylic acid (S)-1-naphthalen-1-yl-ethyl ester [ No CAS ]
Cyclohexanecarboxylic acid (R)-1-naphthalen-1-yl-ethyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 7379 - 7385.

11
[ 22651-87-2 ]
[ 56-81-5 ]
Cyclohexanecarboxylic acid (R)-2,3-dihydroxy-propyl ester [ No CAS ]
Cyclohexanecarboxylic acid (S)-2,3-dihydroxy-propyl ester [ No CAS ]

References: [1]Tetrahedron Asymmetry,2004,vol. 15,p. 3551 - 3559.

12
[ 348641-42-9 ]
[ 22651-87-2 ]
LUF₅₉₈₁ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 828 - 834.

13
[ 1012055-25-2 ]
[ 22651-87-2 ]
[ 98-89-5 ]
(Z)-N-(6-(cyclohexanecarbonyloxyamino)-6-oxohexyl)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	In tetrahydrofuran; N,N-dimethyl-formamide; at 20℃; for 4h;	EXAMPLE 15: Preparation of (Z)-7V-(6-(cyclohexanecarbonyloxyamino)-6- oxohexyl)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-lH- pyrrole-3-carboxamide (Compound 21)Cyclohexanecarboxylic anhydride (5 mL) and cyclohexanecarboxylic acid (150 mg, 1.17 mmol) was added to a solution of compound 4 (500 mg, 1.17 mmol) in <n="68"/>THF (120ml) and DMF (5 mL). The solution was stirred at room temperature for 4 h. THF was removed in vacuo, and then water (100 mL) was added. The mixture was adjusted to pH 7-8 with saturated aqueous NaHCθ3. The resulting solid was collected by filtration, washed with water for three times, dried and purified by preparative HPLC to give product 21 as a yellow solid (100 mg, 13%). LCMS: 539 [M+l]+, 1H NMR (DMSO-(Z6): δ 1.32 (m, 7H), 1.53 (m, 5H), 1.66 (m, 2H), 1.85 (m, 2H), 2.11 (t, J= 6.45 Hz, 2H), 2.39 (s, 3H), 2.41 (s,3H), 3.20 (m, 2H), 6.85 (m,2H), 7.71 (m, 3H) , 10.89 (s, IH), 11.54 (s, 1H),13.67 (s, IH).

References: [1]Patent: WO2008/33743,2008,A1 .Location in patent: Page/Page column 66-67.

14
[ 1012055-25-2 ]
[ 22651-87-2 ]
(Z)-N-(6-(cyclohexanecarbonyloxyamino)-6-oxohexyl)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%		Cyclohexanecarboxylic anhydride (5 mL) and cyclohexanecarboxylic acid (150 mg, 1.17 mmol) was added to a solution of compound 4 (500 mg, 1.17 mmol) in TηF (120ml) and DMF (5 mL). The solution was stirred at room temperature for 4 h. TηF was removed in vacuo, and then water (100 mL) was added. The mixture was adjusted to pη 7~8 with saturated aqueous NaHCO3. The resulting solid was collected by filtration, washed with water for three times, dried and purified by <n="213"/>preparative HPLC to give product 21 as a yellow solid (100 mg, 13%). LCMS: 539 [M+l]+, 1H NMR (DMSO-J6): δ 1.32 (m, 7H), 1.53 (m, 5H), 1.66 (m, 2H), 1.85 (m, 2H), 2.11 (t, J= 6.45 Hz, 2H), 2.39 (s, 3H), 2.41 (s,3H), 3.20 (m, 2H), 6.85 (m,2H), 7.71 (m, 3H) , 10.89 (s, IH), 11.54 (s, 1H),13.67 (s, IH).

References: [1]Patent: WO2008/33747,2008,A2 .Location in patent: Page/Page column 211-212.

15
[ 22651-87-2 ]
[ 145918-75-8 ]
(-)-(2S,4S)-1-[2-(hydroxymethyl)-1,3-dioxolan-4-yl]-4-N-cyclohexyl-cytosine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2249 - 2253.

16
[ 14155-67-0 ]
[ 22651-87-2 ]
[ 903573-97-7 ]

Yield	Reaction Conditions	Operation in experiment
68%		Compound 6d: N-3-cyclohexanecarboxylcycloxobuxidine-F 6dor(20S)-3-(cyclohexanecarboxylamino)-9,19-cyclo-4α-hydroxymethyl-4,14α-dimethyl-20-dimethylamino-5α,9-pregnan-16α-ol-11-one 6d To a solution of 300 mg (0.69 mmol, 1.0 eq) of cycloxobuxidine-F 5 in 10 ml of methanol are added 182 mg (0.76 mmol, 1.1 eq) of <strong>[22651-87-2]cyclohexanecarboxylic acid anhydride</strong>. After 4 hours of agitation at room temperature, the mixture is neutralized with several drops of a 10% sodium bicarbonate solution (pH=8), then alkalinized with 50 ml of a 10% ammonia solution (pH=10) and extracted with 3×40 ml of dichloromethane. The recombined organic phases are successively washed with 30 ml of a sodium chloride saturated aqueous solution, dried on anhydrous sodium sulfate and evaporated under a vacuum. The residue is chromatographed on a Merck activity II-III alumina column (eluent: 99.7/0.3 dichloromethane/methanol then 98/2 dichloromethane/methanol) to yield 225 mg of 6d in the form of a colorless powder after trituration in acetone with a yield of 68%.MP ( C.): 293[α]D=+61.9 (c=1.09; 25 C., CHCl3)Elemental analysis: calculated for C33H54N2O4: C, 73.02; H, 10.03; N, 5.16; O, 11.79. measured: C, 72.76; H, 9.94; N, 5.07; O, 11.68.IR (CHCl3) υ(cm-1): 3434 (OH, NH); 1650 (CO); 1650 and 1512 (CONH); 1050 (C-OH).Mass (ESI): m/z: 543.4 ([M+H], 100); 544.5 (85).HRMS (ESI) calculated for C33H55N2O4 m/z=543.4162; measured: 543.4128.

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5311 - 5323.
[2]Patent: US2012/40930,2012,A1 .Location in patent: Page/Page column 30.

17
[ 645395-99-9 ]
[ 22651-87-2 ]
phosphoric acid mono-{2-[(1-cyclohexyl-methanoyl)-amino]-3-phenyl-propyl} ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%		To an ether solution (5 mL) of cyclohexanecarboxylic acid (250 mg, 1.95 mmol) was added pyridine (0.5 mL) and cyclohexanecarbonyl chloride (286 mg, 0.261 mL, 1.95 MMOL). After 10 h, the suspension was diluted with ether (20 mL), washed with ice-cold 5% HCl solution (1x50 mL) and concentrated NaHCO3 solution (1x50 mL) and dried over Na2S04. All solvent was removed in vacua to give 350 mg of <strong>[22651-87-2]cyclohexanecarboxylic anhydride</strong> as A colorless oil. A portion of the <strong>[22651-87-2]cyclohexanecarboxylic anhydride</strong>. (226 mg, 0. 948 mmol) was added to a sodium carbonate solution (1 M, 2 mL) of the aminophosphate 21a (110 mg, 0.412 mmol). After 15 h, it was acidified to PH#1 by addition of concentrated HCI solution at 0 C. Preparative HPLC purification afforded 50 mg (36% yield) of the title compound 25-17. 1H NMR (CD3OD) : δ 7. 27-7. 1 (5H, m), 6.67 (1H, br d), 4.34 (1H, br s), 4.08 (1H, m), 3.96 (1H, m), 2.90 (1H, dd, J=14.4, 6.6 Hz), 2. 78 (1H, dd, J=14.9, 9 Hz), 2.10 (1H, br t), 1.79-1. 51 (5H, m), 1. 33-1. 02 (5H, m); LCMS (ESP): 342 (M+H+) ; 340 (M-H)-.
36%		A portion of the <strong>[22651-87-2]cyclohexanecarboxylic anhydride</strong> (226 mg, 0.948 mmol) was added to a sodium carbonate solution (1 M, 2 mL) of the aminophosphate 21a (110 mg, 0.412 mmol). After 15 h, it was acidified to pH-1 by addition of concentrated HCl solution at 0 C. Preparative HPLC purification afforded 50 mg (36% yield) of the title compound 25-17. 1H NMR (CD3OD): δ 7.27-7.1 (5H, m), 6.67 (1H, br d), 4.34 (1H, br s), 4.08 (1H, m), 3.96 (1H, m), 2.90 (1H, dd, J=14.4, 6.6 Hz), 2.78 (1H, dd, J=14.9, 9 Hz), 2.10 (1H, br t), 1.79-1.51 (5H, m), 1.33-1.02 (5H, m); LCMS (ESP): 342 (M+H+); 340 (M-H)-.

References: [1]Patent: WO2004/87720,2004,A1 .Location in patent: Page 57.
[2]Patent: US2005/250742,2005,A1 .Location in patent: Page/Page column 37-38.

18
[ 39687-95-1 ]
[ 22651-87-2 ]
5-cyclohexyloxazole-4-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 0 - 20℃; for 11h;	Reference Example 1: Production of 2-cyclohexyl-1-methoxycarbonyl-2-oxo-ethylammonium; chloride; [Show Image] To DMF (N,N-dimethylformamide) (10.0 mL) solution of methylisocyanoate (3.11 g) and cyclohexanoic acid anhydride (8.20 g, 1.1 equivalent), DBU (1,8-diazabicyclo[5.4.0]-7-undecene) (4.7 mL, 1.0 equivalent) was added dropwise at 0C. After stirring at room temperature for 11 hours, the reaction solution was diluted with water, extracted with n-hexane-ethyl acetate (5:1), and the organic phase was separated. Then, the organic phase was washed with saturated salt water, 1 mol/L hydrochloric acid, saturated sodium hydrogen carbonate water and saturated salt water in that order, and then dried over anhydrous sodium sulfate. Then, precipitates were filtered, and the filtrate was concentrated under reduced pressure. The resulting crude product was recrystallized from n-hexane-ethyl acetate to obtain a product (5.00 g, 75%). Melting point: 97.5-101C IR (KBr) 2931, 2852, 1719, 1599, 1199 cm-1; 1H-NMR (400 MHz, CDCl3) δ 1.26-1.89 (m, 10H, c-Hex-CH2), 3.45-3.48 (m, 1H, c-Hex-H), 3.91 (s, 3H, CO2CH3) 7.74 (s, 1H, OCHN); 13C-NMR (100MHz, CDCl3) δ 25.7, 25.9, 30.6,35.4, 51.9, 125.2, 148.6, 162.6, 164.1; HRMS (FAB, NBA) Calcd. for C11H16NO3: 210.1130 (M++1). Found: 210.1119.

References: [1]Tetrahedron Asymmetry,2008,vol. 19,p. 2816 - 2828.
[2]Heterocycles,2009,vol. 77,p. 629 - 634.
[3]Patent: EP1650185,2006,A1 .Location in patent: Page/Page column 14-15.

19
tetrahydro-1-(5-cyclohexyl-1,3,4-thiadiazol-2-yl)-3-allyl-6-hydroxy-2(1H)-pyrimidinone [ No CAS ]
[ 22651-87-2 ]
tetrahydro-1-(5-cyclohexyl-1,3,4-thiadiazol-2-yl)-3-allyl-6-cyclohexylcarbonyloxy-2(1H)-pyrimidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With o-toluenesulfonic acid; In benzene;	EXAMPLE 20 Preparation of Tetrahydro-1-(5-cyclohexyl-1,3,4-thiadiazol-2-yl)-3-allyl-6-cyclohexylcarbonyloxy-2(1H)-pyrimidinone. Tetrahydro-1-(5-cyclohexyl-1,3,4-thiadiazol-2-yl)-3-allyl-6-hydroxy-2(1H)-pyrimidinone (0.1 mole), cyclohexane carboxylic anhydride (0.11 mole), toluenesulfonic acid (0.05 gram) and benzene (100 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture is heated on a steam bath with stirring for a period of about 2 hours. After this time the reaction mixture is cooled to room temperature and is stripped of solvent under reduced pressure leaving a residue. The residue is recrystallized to yield the desired product tetrahydro-1-(5-cyclohexyl-1,3,4-thiadiazol-2-yl)-3-allyl-6-cyclohexylcarbonyloxy-2(1H)-pyrimidinone.

References: [1]Patent: US4004912,1977,A .

20
[ 59066-96-5 ]
[ 22651-87-2 ]
[ 59293-37-7 ]

Yield	Reaction Conditions	Operation in experiment
	With o-toluenesulfonic acid; In benzene;	EXAMPLE 20 Preparation of Tetrahydro-1-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)-3-allyl-6-cyclohexylcarbonyloxy-2(1H)-pyrimidinone Tetrahydro-1-(5-methylsulfonyl-1,3,4-thiadiazol-2yl)-3-allyl-6-hydroxy-2(1H)-pyrimidinone (0.1 mole), cyclohexane carboxylic anhydride (0.11 mole), toluenesulfonic acid (0.05 gram) and benzene (100 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture is heated on a stream bath with stirring for a period of about 2 hours. After this time the reaction mixture is cooled to room temperature and is stripped of solvent under reduced pressure leaving a residue. The residue is recrystallized to yield the desired product tetrahydro-1-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)-3-allyl-6-cyclohexylcarbonyloxy-2(1H)-pyrimidinone.

References: [1]Patent: US4006009,1977,A .

21
[ 136-01-6 ]
[ 2719-27-9 ]
[ 22651-87-2 ]

References: [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 3993 - 4000.

22
[ 22651-87-2 ]
disodium 1-sulfonylcyclohexanecarboxylate [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 3993 - 4000.

23
[ 2719-27-9 ]
[ 22651-87-2 ]

Yield	Reaction Conditions	Operation in experiment
	With water; triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere;	General procedure: TCCA (0.256 g, 1.1 mmol) was portionwise added over a period of 1-2 min to a solution of an aldehyde (1.1 mmol) in 3.25 mL dichloromethane, under dry argon atmosphere and at room temperature. The resulting suspension was stirred at room temperature and under dry argon. The reaction was monitored by TLC until disappearance of the aldehyde. Then the reaction mixture was cooled to 0 C and were added water (1.0 mmol) and NEt3 (0.202 g, 2.0 mmol). After completion of the additions, the reaction mixture left to stir at room temperature until disappearance of the acyl chloride, monitored by TLC. For the products 4a-4g, the solvent was evaporated under reduced pressure and the residue purified by flash chromatography. For the products 4h-4l the reaction mixture was washed three times with a solution of 5 % HCl and then three times with a solution of 5 % NaHCO3; the organic phase was dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure providing the desired anhydride.

References: [1]Tetrahedron Letters,2008,vol. 49,p. 5322 - 5323.
[2]Advanced Synthesis and Catalysis,2013,vol. 355,p. 3137 - 3140.
[3]Tetrahedron Letters,2017,vol. 58,p. 2533 - 2536.

24
[ 93-54-9 ]
[ 22651-87-2 ]
[ 501-52-0 ]
(1R)-1-phenylpropyl 3-phenylpropanoate [ No CAS ]
(1R)-1-phenylpropyl cyclohexanecarboxylate [ No CAS ]
[ 1565-74-8 ]
[ 613-87-6 ]

References: [1]Heterocycles,2009,vol. 77,p. 801 - 810.

25
[ 73834-77-2 ]
[ 22651-87-2 ]
[ 1269418-57-6 ]

Yield	Reaction Conditions	Operation in experiment
83%		General procedure: A solution of 11 (50 mg, 0.27 mmol) and carbxylic anhydride (0.54 mmol) in anhydrous pyridine (5 ml) was stirred at room temperature for 5 h. Saturated aqueous Na2CO3 solution was added and the mixture was stirred at room temperature for 1 h and extracted twice with ethyl acetate. The extracts were dried with anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel to afford (β-carbolin-3-yl)alkanecarboxamide (12b-e). To 12 in anhydrous THF (5 ml) was added LiAlH4 (25 mg, 0.66 mmol), and the mixture was refluxed for 2 h. A piece of ice (1 ml) was added, and the mixture was stirred at room temperature for 2 h and then filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel to afford the title compounds (1b-e).

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 636 - 646.

26
[ 22651-87-2 ]
[ 62-53-3 ]
[ 2719-26-8 ]