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[ CAS No. 6246-06-6 ] {[proInfo.proName]}

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Chemical Structure| 6246-06-6
Chemical Structure| 6246-06-6
Structure of 6246-06-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6246-06-6 ]

CAS No. :6246-06-6 MDL No. :MFCD17015894
Formula : C4H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SWYHWLFHDVMLHO-UHFFFAOYSA-N
M.W : 88.11 Pubchem ID :11521066
Synonyms :
Chemical Name :Oxetan-3-ylmethanol

Calculated chemistry of [ 6246-06-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 21.47
TPSA : 29.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.22
Log Po/w (XLOGP3) : -0.57
Log Po/w (WLOGP) : -0.37
Log Po/w (MLOGP) : -0.57
Log Po/w (SILICOS-IT) : 0.77
Consensus Log Po/w : 0.09

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.04
Solubility : 96.3 mg/ml ; 1.09 mol/l
Class : Highly soluble
Log S (Ali) : 0.42
Solubility : 233.0 mg/ml ; 2.64 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.05
Solubility : 99.3 mg/ml ; 1.13 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.11

Safety of [ 6246-06-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P362+P364-P403+P233-P501 UN#:1760
Hazard Statements:H302-H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6246-06-6 ]

* 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.

  • Downstream synthetic route of [ 6246-06-6 ]

[ 6246-06-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 6246-06-6 ]
  • [ 1305207-52-6 ]
YieldReaction ConditionsOperation in experiment
54% With Dess-Martin periodane In dichloromethane at 20℃; for 0.166667h; 18 Oxetane-3-carbaldehyde. To a solution of oxetan-3-ylmethanol (215 mg, 2.440 mmol) in dichloromethane (8.1 mL) at room temperature was added Dess- Martin Periodinane (1242 mg, 2.93 mmol) in two portions over 5 min. After 10 min, the flask was fitted with a shortpath distillation head. The product distilled at ca. 110 °C to give 114 mg (54%). 1H NMR (CDCl3) δ: 9.98 (d, J=2.3 Hz, 1H), 4.83-4.94 (m, 4H), 3.83 (ttd, J=8.3, 6.1, 2.3 Hz, 1H).
With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 2.5h; 1 Compound 180.1. 4-Methyl-2-(oxetan-3-yI)-lH-imidazole. Dess-Martin reagent (4.33g, 10.21mmol) was added to a solution of oxetan-3-ylmethanol (0.9g, 10.21 mmol) in CH2CI2 (10 mL) at 0 °C. The mixture was stirred at 0 °C for 30 minutes and at room temperature for 2 hours. CH2C12 was then removed under reduced pressure. The residue was dissolved in EtOH (10 mL). NH4OH (5 mL) was added, followed by 2-oxopropanal (40% in water, 2.76 mL, 15.32 mmol). The mixture was stirred at room temperature for 4 hours. Water (l OmL) was added to the mixture and the mixture was lyophilized. The dried residue was purified with column chromatography (2.5% MeOH to 5% MeOH in CH2CI2) to give the title pro steps), m/z (ES+) 139 (M+H)+.
With Dess-Martin periodane In dichloromethane at 20℃; 6 Oxetane-3-carbaldehyde XXVIII To a round-bottomed flask equipped with a stirring bar, oxetan-3-ylmethanol (2.00 g, 22.7 mmol) was dissolved in DCM (50 mL) and Dess-Martin periodinane (10.67 g, 28.38 mmol) was added in one portion. The reaction mixture was stirred at RT overnight. The solids were filtered through celite, and washed with DCM (3 mL*5). The filtrate was removed and concentrated in vacuo and the resulting crude oxetane-3-carbaldehyde XXVIII was used in the next step directly.
With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 2.5h; Compound 180.1. 4-Methyl-2-(oxetan-3-yl)-lH-imidazole Compound 180.1. 4-Methyl-2-(oxetan-3-yl)-lH-imidazole. Dess-Martin reagent (4.33g, 10.21mmol) was added to a solution of oxetan-3-ylmethanol (0.9g, 10.21 mmol) in CH2CI2 (10 mL) at 0 °C. The mixture was stirred at 0 °C for 30 minutes and at room temperature for 2 hours. CH2CI2 was then removed under reduced pressure. The residue was dissolved in EtOH (10 mL). NH4OH (5 mL) was added, followed by 2-oxopropanal (40% in water, 2.76 mL, 15.32 mmol). The mixture was stirred at room temperature for 4 hours. Water (lOmL) was added to the mixture and the mixture was lyophilized. The dried residue was purified with column chromatography (2.5% MeOH to 5% MeOH in CH2CI2) to give the title pro s), m/z (ES+) 139 (M+H)+.
With Dess-Martin periodane In dichloromethane at 20℃; 6 Oxetane-3-carbaldehyde XXVIII: To a round-bottomed flask equipped with a stirring bar, oxetan-3-ylmethanol (2.00 g, 22.7 mmol) was dissolved in DCM (50 mL) and Dess-Martin periodinane (10.67 g, 28.38 mmol) was added in one portion. The reaction mixture was stirred at RT overnight. The solids were filtered through celite, and washed with DCM (3 mL x 5). The filtrate was removed and concentrated in vacuo and the resulting crude oxetane-3-carbaldehyde XXVIII was used in the next step directly.
With piridinium dichromate In dichloromethane at 20℃; for 16h; 81 To a stirred, room temperature solution of oxetan-3-ylmethanol (2.20 g, 24.97 mmol) in dichloromethane (110 mL) was added solid pyridinium dichromate (5.87 g, 15.6 mmol) in five portions. The resulting black mixture was stirred at room temperature for 16 hours. The deep brown suspension was then filtered through a silica gel pad and the filter cake rinsed with dichloromethane (8×120 mL). The combined dichloromethane filtrates were partially concentrated under reduced pressure at room temperature (27-30° C.) to afford oxetane-3-carbaldehyde (81a, 3 g, 26% yield) as a colorless solution, 18.7 wt % solution in dichloromethane by NMR. The solution was dried over magnesium sulfate, filtered and used immediately in the next step. 1H NMR (400 MHz, CDCl3) δ 9.95 (d, J=2.4 Hz, 1H), 4.87 (m, 4H), 3.81 (m, 1H).
With Dess-Martin periodane In dichloromethane at 20℃; 6 Oxetane-3-carbaldehyde XXVIII [0307] Oxetane-3-carbaldehyde XXVIII: To a round-bottomed flask equipped with a stirring bar, oxetan-3-ylmethanol (2.00 g, 22.7 mmol) was dissolved in DCM (50 mL) and Dess-Martin periodinane (10.67 g, 28.38 mmol) was added in one portion. The reaction mixture was stirred at RT overnight. The solids were filtered through celite, and washed with DCM (3 mL x 5). The filtrate was removed and concentrated in vacuo and the resulting crude oxetane-3-carbaldehyde XXVIII was used in the next step directly.
With Dess-Martin periodane In dichloromethane at 25℃; for 2h; 30; 31.1 Step 1: oxetane-3-carbaldehyde a solution of oxetan-3-ylmethanol (2 g, 22.70 mmol, 1.00 eq.) in dichloromethane (20 mL) and l,l,l-triacetoxy-l, l-dihydro-l,2- benziodoxol-3(lH)-one (1 1.7 g, 27.59 mmol, 1.00 eq.) was stirred for 2 hours at 25 °C. The solids were filtered out and the mixture was concentrated under vacuum to give 2.1 g (crude) of oxetane-3-carbaldehyde as yellow oil.
With Dess-Martin periodane In dichloromethane at 20℃; for 2h; Inert atmosphere; 3,3-Difluorocyclobutanecarbaldehyde (21) General procedure: To a solution of (3,3-difluorocyclobutyl)methanol (4.0 g, 32.8 mmol) in dichloromethane (109 ml) at room temperature was added Dess-Martin Periodinane (16.7 g, 39.3 mmol). After 2 h, the reaction was diluted with two volumes of ether and treated with sodiumthiosulfate (32 g) in water (160 mL). After stirring at room temperature for 10 min, the layers were separated. The ethereal was washed with saturated sodium bicarbonate (2X), dried over magnesium sulfate, and filtered. The resulting solution was concentrated via distillation of the solvent through a short path distillation apparatus. The distillation was discontinued when 6.56 g remained in the boiling flask. Integration of the 1H NMR showed product as a 28.4 wt% solution in diethyl ether (1.86 g, 47% yield). The material was directly used without further concentration
With Dess-Martin periodane In dichloromethane at 20℃; 6.XXVIII Oxetane-3-carbaldehyde XXVIII To a round-bottomed flask equipped with a stirring bar, oxetan-3-ylmethanol (2.00 g, 22.7 mmol) was dissolved in DCM (50 mL) and Dess-Martin periodinane (10.67 g, 28.38 mmol) was added in one portion. The reaction mixture was stirred at RT overnight. The solids were filtered through celite, and washed with DCM (3 mL x 5). The filtrate was removed and concentrated in vacuo and the resulting crude oxetane-3-carbaldehyde XXVIII was used in the next step directly.
With Dess-Martin periodane In dichloromethane at 25℃; for 2h; 30.1; 31.1 Step 1: oxetane-3-carbaldehyde: a solution of oxetan-3-ylmethanol (2 g, 22.70 mmol, 1.00 eq.) in dichloromethane (20 mL) and 1,1,1-triacetoxy-1,1-dihydro-1,2- benziodoxol-3(1H)-one (11.7 g, 27.59 mmol, 1.00 eq.) was stirred for 2 hours at 25°C. The solids were filtered out and the mixture was concentrated under vacuum to give 2.1 g (crude) of oxetane-3-carbaldehyde as yellow oil.
With Dess-Martin periodane In dichloromethane at 25℃; for 2h; 30.1; 31.1 Step 1: oxetane-3-carbaldehyde: a solution of oxetan-3-ylmethanol (2 g, 22.70 mmol, 1.00 eq.) in dichloromethane (20 mL) and 1,1,1-triacetoxy-1,1-dihydro-1,2- benziodoxol-3(1H)-one (11.7 g, 27.59 mmol, 1.00 eq.) was stirred for 2 hours at 25°C. The solids were filtered out and the mixture was concentrated under vacuum to give 2.1 g (crude) ofoxetane-3-carbaldehyde as yellow oil.
26 %Spectr. With piridinium dichromate In dichloromethane at 20℃; for 16h;
With piridinium dichromate In dichloromethane at 25℃; for 16h; 9 Compound 9.1: To a solution of oxetan-3-ylmethanol (0.50 g, 5.68 mmol, 1 equivalent) in DCM (25 mL) was added pyridinium dichromate (1.39 g, 3.69 mmol, 0.65 equivalent) in five portions. After stirred at 25° C. for 16 hours, the resulting black mixture was filtered through a silica gel pad and washed with DCM (8*10 mL), dried over sodium sulfate then concentrated under reduced pressure to give the oxetane-3-carbaldehyde (9.1) as a yellow oil (0.38 g, yield=58.7%). This material was used without further purification.
With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 1.5h; 29.1 Step 1: Step 1: Preparation of (S,E)-2-methyl-N-(oxetan-3-ylmethylene)propane-2-sulfinamide To a solution of oxetan-3-ylmethanol (2.0 g, 22.7 mmol) in DCM (20 mL) at 0° C. was added Dess-Martin periodinane (14.4 g, 34.0 mmol) portion wise. The ice bath was removed, and the resulting suspension was stirred at room temperature for 1.5 h. The reaction mixture was filtered through Celite, and the filtrate was partially concentrated under reduced pressure (water bath temperature 10-15° C. to prevent evaporation of aldehyde) so that approximately 10 mL of DCM remained. The resulting suspension was filtered again through Celite, and the filtered solid was rinsed with a minimum amount of DCM. To the filtrate was washed with added additional DCM (10 mL), and the resulting mixture was cooled to 0 C with an ice bath. (S)-2-methylpropane-2-sulfinamide (3.0 g, 25.0 mmol) was added portion wise, followed by titanium isopropoxide (9.7 g, 34.1 mmol). The ice bath was removed, and the reaction mixture was stirred at room temperature for 1 hour. The mixture was carefully poured into saturated aqueous NaHCO3 (gas evolution) and then stirred vigorously at room temperature for 30 min. The suspension was filtered through Celite and the filter cake was washed with DCM (20 mL). The filtrate was transferred to a separatory funnel, the layers were separated, and the combined were dried over Na2SO4 and concentrated under reduced pressure. The remaining viscous oil was purified with silica gel (0-50% ethyl acetate in hexanes) to provide the desired product (1.2 g, 6.3 mmol) as a viscous yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 8.17 (d, J=4.3 Hz, 1H), 4.80 (ddd, J=2.7, 6.0, 8.4 Hz, 2H), 4.65 (dt, J=6.1, 14.9 Hz, 2H), 4.11 (ttd, J=4.3, 6.3, 8.4 Hz, 1H), 1.14 (s, 10H).
With Dess-Martin periodane In dichloromethane at 20℃; for 3.25h; Cooling with ice; 1 Synthesis of 3-((1R,5S,9r)-9-methoxy-3-(oxetan-3-ylmethyl)-3-azabicyclo[3.3.1]nonan-9-yl)benzamide (S)-2-hydroxysuccinate Synthesis of 3-((1R,5S,9r)-9-methoxy-3-(oxetan-3-ylmethyl)-3-azabicyclo[3.3.1]nonan-9-yl)benzamide (S)-2-hydroxysuccinate To a ice cold solution of oxetan-3-yl methanol (52 μL, 0.64 mmol) in dichloromethane (2 mL) was added Dess-Martin periodinane (273 mg, 0.64 mmol) and the reaction mixture was stirred for 15 minutes then warmed to room temperature and stirred for 3 hours to give a solution of oxetane-3-carbaldehyde which was used directly. To a mixture of 3-((1R,5S,9r)-9-methoxy-3-azabicyclo[3.3.1]nonan-9-yl)benzamide hydrochloride (100 mg, 0.32 mmol) in dichloromethane (3 mL) was added triethylamine (45 μL, 0.32 mmol), followed by a solution of oxetane-3-carbaldehyde (0.64 mmol) in dichloromethane (2 mL) and the reaction mixture was stirred for 30 minutes at room temperature. Sodium triacetoxyborohydride (205 mg, 0.97 mmol) was added and the reaction mixture was stirred for 18 hours at room temperature. The mixture was diluted with dichloromethane and washed with aqueous sodium hydrogen carbonate solution. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica chromatography, eluting with 4% ammonia/methanol in dichloromethane and then further purified by preparative HPLC. The acetonitrile was removed under reduced pressure and the aqueous phase freeze dried to give 3-((1R,5S,9r)-9-methoxy-3-(oxetan-3-ylmethyl)-3-azabicyclo[3.3.1]nonan-9-yl)benzamide (50 mg, 45% yield).
With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 2h; oxetane-3-carbaldehyde To a solution of oxetan-3-ylmethanol [CAS-RN 6246-06-6] (0.70 g, 7.94 mmol) in dichloromethane (20 ml) at 0 °C was added Dess-Martin periodinane (2.97 g, 7.15 mmol). After stirring at rt for 2 h, the reaction mixture was quenched with satd. aq. sodium thiosulfate solution (50 ml). The solid was filtered off and the filtrate was extracted three times with dichloromethane (50 ml each). The combined organic layers were washed with brine (100 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate 1:3) to yield 0.50 g (90 % purity, 66 % yield) of the title compound.1H-NMR (300 MHz, DMSO-d6) d [ppm]: 3.82 - 3.93 (m, 1H), 4.64 - 4.73 (m, 4H), 9.83 (s, 1H).
With piridinium dichromate In dichloromethane at 20℃; 12.1 Step 1: oxetane-3-carbaldehyde A mixture of oxetan-3-ylmethanol (7.0 g, 79.45 mmol, 1.0 equiv), Pyridinium Dichromate (19.4 g, 54.57 mmol, 0.65 equiv) in DCM (200 mL) was stirred at room temperature overnight. The mixture was filtered. The filtrate was used directly in the next step.

Reference: [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2015/54103, 2015, A1 Location in patent: Page/Page column 33
[2]Current Patent Assignee: SAGIMET BIOSCIENCES INC. - WO2014/8197, 2014, A1 Location in patent: Page/Page column 207; 208
[3]Current Patent Assignee: KRONOS BIO INC - US2015/175616, 2015, A1 Location in patent: Paragraph 0283; 0284
[4]Current Patent Assignee: SAGIMET BIOSCIENCES INC. - WO2015/95767, 2015, A1 Location in patent: Page/Page column 222; 223
[5]Current Patent Assignee: KRONOS BIO INC - WO2015/100217, 2015, A1 Location in patent: Page/Page column 118; 119
[6]Current Patent Assignee: PFIZER INC - US2015/361067, 2015, A1 Location in patent: Paragraph 0599
[7]Current Patent Assignee: KRONOS BIO INC - WO2016/10809, 2016, A1 Location in patent: Paragraph 0307
[8]Current Patent Assignee: YUMANITY THERAPEUTICS INC - WO2016/105485, 2016, A2 Location in patent: Paragraph 0211
[9]Degnan, Andrew P.; Maxwell, Darrell; Balakrishnan, Anand; Brown, Jeffrey M.; Easton, Amy; Gulianello, Michael; Hanumegowda, Umesh; Hill-Drzewi, Melissa; Miller, Regina; Santone, Kenneth S.; Senapati, Arun; Shields, Eric E.; Sivarao, Digavalli V.; Westphal, Ryan; Whiterock, Valerie J.; Zhuo, Xiaoliang; Bronson, Joanne J.; Macor, John E. [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 24, p. 5871 - 5876]
[10]Current Patent Assignee: KRONOS BIO INC - WO2016/172117, 2016, A1 Location in patent: Page/Page column 48
[11]Current Patent Assignee: YUMANITY THERAPEUTICS INC - WO2017/19589, 2017, A1 Location in patent: Paragraph 0185
[12]Current Patent Assignee: YUMANITY THERAPEUTICS INC - WO2017/112853, 2017, A1 Location in patent: Paragraph 0185
[13]Kung, Pei-Pei; Bingham, Patrick; Brooun, Alexei; Collins, Michael; Deng, Ya-Li; Dinh, Dac; Fan, Connie; Gajiwala, Ketan S.; Grantner, Rita; Gukasyan, Hovhannes J.; Hu, Wenyue; Huang, Buwen; Kania, Robert; Kephart, Susan E.; Krivacic, Cody; Kumpf, Robert A.; Khamphavong, Penney; Kraus, Manfred; Liu, Wei; Maegley, Karen A.; Nguyen, Lisa; Ren, Shijian; Richter, Dan; Rollins, Robert A.; Sach, Neal; Sharma, Shikhar; Sherrill, John; Spangler, Jillian; Stewart, Albert E.; Sutton, Scott; Uryu, Sean; Verhelle, Dominique; Wang, Hui; Wang, Shuiwang; Wythes, Martin; Xin, Shuibo; Yamazaki, Shinji; Zhu, Huichun; Zhu, Jinjiang; Zehnder, Luke; Edwards, Martin [Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 650 - 665]
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  • 2
  • [ 6246-06-6 ]
  • [ 114012-41-8 ]
YieldReaction ConditionsOperation in experiment
86% With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium hydrogencarbonate; potassium bromide In dichloromethane; water at 0 - 20℃; for 13h; 1.5 (5) 3-oxetane methanol to prepare 3-oxetanecarboxylic acid, the specific reaction formula is as follows: The white solid obtained in the step (4) (50 g, 0.57 mol) was dissolved in dichloromethane (1.2 L), and aqueous potassium bromide (13 g, 0.12 mol, water 430 mL) was added.Tempo (1.5 g, 0.012 mol), aqueous potassium hydrogencarbonate (115 g, 1.2 mol), stirred for 10 min after the addition.The system was ice-cooled, cooled to 0-5 ° C, and slowly added sodium hypochlorite aqueous solution (10%, 800 mL) to keep the system temperature below 10 ° C.After the completion of the dropwise addition, the temperature was maintained for 3 hours, and the temperature was naturally raised, and the reaction was continued at room temperature for 10 hours.After completion of the reaction, excess sodium hypochlorite was quenched with aqueous sodium thiosulfate (71 g, 0.29 mol, water 120 mL).The reaction system was adjusted to a pH of more than 12 with a 50% aqueous sodium hydroxide solution, and the aqueous phase was extracted once more with dichloromethane.The two dichloromethanes were discarded.The aqueous phase is adjusted to pH less than 2 with hydrochloric acid, then extracted three times with dichloromethane, and the organic phase is combined three times.The organic layer was concentrated to give 42 g of the desired compound, 3-oxetanecarboxylic acid, yield 86%.
81% With Dess-Martin periodane In dichloromethane at 20℃; for 2h; Cooling with ice; 1.6 (6) Preparation of 3-oxetanecarboxylic acid from 3-oxetane methanol, The specific reaction formula is as follows: The target obtained in the step (5) (20 g, 0.23 mol)Soluble in dichloromethane (2L),Ice bath, stirring,One part was added to Dess Martin oxidant (195g, 0.46mol).The system was naturally warmed to room temperature and stirring was continued for 2 hours.10% sodium thiosulfate (200 mL) was added dropwise.Add 2L of water,Layering, extracting the aqueous phase with dichloromethane, combining the organic phases,Washed three times,Washed with saturated brine, dried, concentrated,The residue was dissolved in 50 mL of petroleum ether.Ice bath,1 mL of ethyl acetate was added dropwise with stirring.After half an hour of filtration, 19 g of a white powder was obtained in a yield of 81%.
55% With ruthenium trichloride; sodium periodate In water; acetonitrile at 20℃; for 20h;
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