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Chemical Structure| 15932-93-1 Chemical Structure| 15932-93-1

Structure of 3-Hydroxycyclobutan-1-one
CAS No.: 15932-93-1

Chemical Structure| 15932-93-1

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Product Details of [ 15932-93-1 ]

CAS No. :15932-93-1
Formula : C4H6O2
M.W : 86.09
SMILES Code : O=C1CC(O)C1
MDL No. :MFCD21604157
InChI Key :VYZHGWJPDGIYDR-UHFFFAOYSA-N
Pubchem ID :22486676

Safety of [ 15932-93-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225
Precautionary Statements:P210-P403+P235
Class:3
UN#:1993
Packing Group:

Application In Synthesis of [ 15932-93-1 ]

* 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 [ 15932-93-1 ]

[ 15932-93-1 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 7647-01-0 ]
  • [ 98485-32-6 ]
  • [ 7732-18-5 ]
  • [ 779-90-8 ]
  • [ 30830-25-2 ]
  • [ 15932-93-1 ]
  • 2
  • [ 15932-93-1 ]
  • [ 20514-71-0 ]
YieldReaction ConditionsOperation in experiment
99% With dihydrogen peroxide; oxalic acid; lithium tetrakis(pentafluorophenyl)borate; In water; 1,2-dichloro-ethane; at 20.0℃; for 9.0h; As shown in Tables 5 and 6, the Baeyer-Villiger oxidation reaction was investigated using various reactive substrates. As the catalyst, a borate salt of Li or Ca was used. In general, although the catalytic activity of a Ca borate salt was higher, since a Li borate salt was a commercially available product, and the amount thereof to be used was small due to its low molecular weight, the Li borate salt was first used (Examples 57, 58, 66 to 71, and 73). However, when the Li borate salt was not sufficient depending on the reactive substrate, and the chemical yield of the product was low, the Ca borate salt was used as the catalyst (Examples 59 to 65, 72, and 74 to 76). In Examples 66 to 72, when a cyclobutanone derivative was used as the reactive substrate, a corresponding lactone was obtained at a high yield in each case. Among the above Examples, in Examples 69 and 70, although an unstable reactive substrate, which had a halogen group at one carbon and a hydroxy group or a siloxy group at the carbon adjacent thereto and which was liable to form an epoxy ring, was used, no epoxidation occurred.Product of Example 67: colorless oil. TLC, Rf=0.1 (hexane-EtOAc=1:1); 1H NMR (CDCl3, 400 MHz) delta 2.54 (d, J=17.8, 1H), 2.58 (brs, 1H), 2.77 (dd, J=17.9, 5.6 Hz, 1H), 4.32 (d, J=10.1 Hz, 1H), 4.43 (dd, J=10.5, 4.6 Hz, 1H), 4.71 (m, 1H).
  • 3
  • N-((5-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)pyridin-2-yl)methyl)-N-phenylpiperidine-4-sulfonamidedihydrochloride [ No CAS ]
  • [ 15932-93-1 ]
  • N-((5-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)pyridin-2-yl)methyl)-1-(3-hydroxycyclobutyl)-N-phenylpiperidine-4-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
43.6% With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20.0℃; for 18.0h; A mixture of N((5-(5-(difluoromethyl)- 1,3 ,4-oxadiazol-2-yl)pyridin-2-yl)methyl)-N-phenylpiperidine- 4-sulfonamide dihydrochioride (0.090 g, 0.172 mmol), <strong>[15932-93-1]3-hydroxycyclobutan-1-one</strong> (0.044 g, 0.517 mmol) and N,N-diisopropylethylamine (0.090 mL, 0.517 mmol) in dichloromethane (5 mL) was treated at the room temperature with sodium triacetoxyborohydride (0.073 g, 0.345 mmol), and stuffed at the same temperature for 18 hr. Then, saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous Mg504, filtered, and concentrated in vacuo. The residue was chromatographed (5i02, 12 g cartridge; methanol / dichloromethane = 0 % to 5 %) to give N((5-(5-(difluoromethyl)- 1,3 ,4-oxadiazol-2-yl)pyridin-2-yl)methyl)- 1 -(3-hydroxycyclob utyl)-N-phenylpiperidine-4-sulfonamide as pale orange solid (0.039 g, 43.6 %).?H NMR (400 MHz, DMSO-d6) oe 9.09 (d, 1 H, J = 2.2 Hz), 8.41 (dd, 1 H, J = 8.2,2.3 Hz), 7.72-7.68 (m, 1.25 H), 7.56 (s, 0.5 H), 7.49 (d, 2 H, J= 7.5 Hz), 7.43 (s, 0.25H), 7.38 - 7.31 (m, 2 H), 7.25 (t, 1 H, J= 7.3 Hz), 5.17 (s, 2 H), 4.93 (m, 1 H), 4.18 (m,0.5 H), 3.78 (m, 0.5 H), 3.00 - 2.80 (m, 2 H), 2.34 (m, 1 H), 2.15 - 2.03 (m, 4 H), 2.00(m, 1 H), 1.90 - 1.54 (m, 6 H); LRMS (ES) mlz 520.4 (M+1).
  • 4
  • methyl 4-((N-(3-chlorophenyl)piperidine-4-sulfonamido)methyl)benzoate hydrochloride [ No CAS ]
  • [ 15932-93-1 ]
  • methyl 4-(((N-(3-chlorophenyl)-1-(3-hydroxycyclobutyl)piperidine)-4-sulfonamido)methyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97.9% With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20.0℃; for 18.0h; A mixture of methyl4-((N-(3-chlorophenyl)piperidine-4- sulfonamido)methyl)benzoate hydrochloride (0.790 g, 1.720 mmol), <strong>[15932-93-1]3-hydroxycyclobutan-1-one</strong> (0.296 g, 3.439 mmol) and N,N-diisopropylethylamine (0.599 mL, 3.439 mmol) in dichloromethane (20 mL) was treated at the room temperature with sodium triacetoxyborohydride (0.729 g, 3.439 mmol), and stirred at the same temperature for 18 hr. Then, saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (Si02, 40 g cartridge; methanol / dichloromethane = 0 % to 5 %) to give methyl4-(((N-(3-chlorophenyl)- 1 -(3-hydroxycyclobutyl)piperidine)-4- sulfonamido)methyl)be nzoate as beige solid (0.830 g, 97.9 %).
  • 5
  • methyl-6-((N-(3-chlorophenyl)piperidine-4-sulfonamido)methyl)nicotinate dihydrochloride [ No CAS ]
  • [ 15932-93-1 ]
  • methyl-6-(((N-(3-chlorophenyl)-1-(3-hydroxycyclobutyl)piperidine)-4-sulfonamido)methyl)nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91.5% With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20.0℃; for 18.0h; A mixture of methyl6-((N-(3-chlorophenyl)piperidine-4- sulfonamido)methyl)nicotinate dihydrochloride (0.780 g, 1.570 mmol), <strong>[15932-93-1]3-hydroxycyclobutan-1-one</strong> (0.270 g, 3.140 mmol) and N,N-diisopropylethylamine (0.820 mL, 4.7 10 mmol) in dichloromethane (20 mL) was treated at the room temperature with sodium triacetoxyborohydride (0.665 g, 3.140 mmol), and stirred at the same temperature for 18 hr. Then, saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (Si02, 40 g cartridge; methanol / dichloromethane = 0 % to 5 %) to give methyl6-(((N-(3-chlorophenyl)- 1 -(3-hydroxycyclobutyl)piperidine)-4- sulfonamido)methyl)ni cotinate as beige solid (0.7 10 g, 91.5 %).
  • 6
  • N-(3-chlorophenyl)-N-(4-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)benzyl)piperidine-4-sulfonamide hydrochloride [ No CAS ]
  • [ 15932-93-1 ]
  • N-(3-chlorophenyl)-N-(4-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)benzyl)-1-(3-hydroxycyclobutyl)piperidine-4-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
39.4% With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20.0℃; for 18.0h; A mixture of N(3-chlorophenyl)-N-(4-(5-(difluoromethyl)- 1,3 ,4-oxadiazol-2-yl)benzyl)piperidine-4- sulfonamide hydrochloride (0.050 g, 0.096 mmol), <strong>[15932-93-1]3-hydroxycyclobutan-1-one</strong> (0.025 g, 0.289 mmol) and N,N-diisopropylethylamine (0.034 mL, 0.193 mmol) in dichioromethane (5 mL) was treated at the room temperature with sodium triacetoxyborohydride (0.041 g, 0.193 mmol), and stirred at the same temperature for 18 hr. Then, saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (Si02, 12 g cartridge; methanol / dichloromethane = 0 % to 5 %) to give N(3-chlorophenyl)-N-(4-(5-(difluoromethyl)- 1,3 ,4-oxadiazol-2-yl)benzyl)- 1 -(3-hydroxy cyclobutyl)piperidine-4-sulfonamide as orange solid (0.021 g, 39.4 %).?H NMR (400 MHz, DMSO-d6) oe 8.04 - 7.95 (m, 2 H), 7.65 (s, 0.25 H), 7.56 - 7.42(m, 3.5 H), 7.41 -7.38 (m, 1.25 H), 7.37 -7.27 (m, 2 H), 5.11 (s, 2 H), 4.93 (m, 1 H),4.20 (m, 1 H), 3.03 - 2.88 (m, 2 H), 2.34 (m, 1 H), 2.16 - 2.05 (m, 4 H), 2.04 - 1.97 (m,2 H), 1.92 - 1.85 (m, 2 H), 1.79 - 1.58 (m, 3 H); LRMS (ES) mlz 553.2 (M÷+1).
  • 7
  • N-(4-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)benzyl)-N-(m-tolyl)piperidine-4-sulfonamide hydrochloride [ No CAS ]
  • [ 15932-93-1 ]
  • N-(4-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)benzyl)-1-(3-hydroxycyclobutyl)-N-(m-tolyl)piperidine-4-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
32.3% With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20.0℃; for 18.0h; A mixture of N(4-(5-(difluoromethyl)- 1,3 ,4-oxadiazol-2-yl)benzyl)-N-(m-tolyl)piperidine-4-sulfonamide hydrochloride (0.090 g, 0.180 mmol), <strong>[15932-93-1]3-hydroxycyclobutan-1-one</strong> (0.047 g, 0.54 1 mmol) and N,N-diisopropylethylamine (0.063 mL, 0.36 1 mmol) in dichloromethane (5 mL) was treated at the room temperature with sodium triacetoxyborohydride (0.076 g, 0.361 mmol), and stirred at the same temperature for 18 hr. Then, saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (Si02, 12 g cartridge; methanol / dichloromethane = 0 % to 5 %) to give N(4-(5-(difluoromethyl)- 1,3 ,4-oxadiazol-2-yl)benzyl)- 1 -(3-hydroxycyclobutyl)-N-(m-tol yl)piperidine-4-sulfonaniide as light yellow solid (0.031 g, 32.3 %).?H NMR (400 MHz, DMSO-d6) oe 7.98 (d, 2 H, J= 6.6 Hz), 7.66 (s, 0.25 H), 7.53 (s,0.5 H), 7.50 (d, 2 H, J= 8.3 Hz), 7.40 (s, 0.25 H), 7.27 -7.16 (m, 3 H), 7.04 (m, 1 H),5.05 (s, 2 H), 4.93 (m, 1 H), 4.14 (m, 0.5 H), 3.75 (m, 0.5 H), 3.19 (m, 1 H), 2.93 (m, 1H), 2.91 - 2.78 (m, 2 H), 2.33 (m, 1 H), 2.25 (s, 3 H), 2.13 - 2.02 (m, 3 H), 1.86 (m, 1H), 1.77 - 1.53 (m, 5 H); LRMS (ES) mlz 533.4 (M+1).
  • 8
  • [ 15932-93-1 ]
  • 5-(tert-butyl)-N-(8-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-5-yl)-1,2,4-oxadiazole-3-carboxamide [ No CAS ]
  • 5-(tert-butyl)-N-(2-(3-hydroxycyclobutyl)-8-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-5-yl)-1,2,4-oxadiazole-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With sodium cyanoborohydride; zinc(II) chloride; In methanol; at 20.0℃; for 4.0h; General procedure: To a solution of 5-(tert-butyl)-N-(8-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)- 2,3,4,5-tetrahydro-1H-benzo[c]azepin-5-yl)-1,2,4-oxadiazole-3-carboxamide (180 mg, 0.36 mmol) and dihydrofuran-3(2H)-one (132 mg, 1.8 mmol) in MeOH (20 mL) were addedNaBH3CN (66 mg, 1.08 mmol) and ZnCl2(246 mg, 1.8 mmol). The mixture was stirred at rt for 16 h. After concentration and diluting with water (30 mL), the mixture was extracted with EtOAc (80 mL x 2). The combined organic layer was washed with H2O (60 mL) andconcentrated. The crude product was purified by prep-HPLC (CH3CN/H2O with 0.05%NH4Hco3as mobile phase) to give 5-(tert-butyl)-N-(8-(2-((1-methyl-1H-pyrazol-4- yl)amino)pyrimidin-4-yl)-2-(oxetan-3-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-5-yl)-1,2,4- oxadiazole-3-carboxamide as a yellow solid (114 mg, yield: 49%). ESI-MS (M+H)+: 544.3.1H NMR (400 MHz, CD3OD) delta: 8.30 (d, J = 5.2 Hz, 1H), 7.92-7.85 (m, 3H), 7.51 (s, 1H), 7.35 (d, J = 8.4 Hz, 1H), 7.11 (d, J = 5.2 Hz, 1H), 5.50 (d, J = 9.6 Hz, 1H), 4.67-4.55 (m, 4H), 3.84-3.70 (m, 3H), 3.80 (s, 3H), 2.95-2.89 (m, 1H), 2.76-2.72 (m, 1H), 2.15-2.12 (m, 1H), 1.95-1.92 (m, 1H), 1.40 (s, 9H).
 

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• Appel Reaction • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Fischer Indole Synthesis • Grignard Reaction • Halogenation • Heat of Combustion • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Jones Oxidation • Lawesson's Reagent • Leuckart-Wallach Reaction • Martin's Sulfurane Dehydrating Reagent • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Alcohols • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Alcohols • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions with Organometallic Reagents • Reformatsky Reaction • Ritter Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Swern Oxidation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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