1-Benzhydrylazetidin-3-ol
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1-Benzhydrylazetidin-3-ol
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CAS No:
18621-17-5
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Formula:
C16H17NO
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Chemical Name:
1-Benzhydrylazetidin-3-ol
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Synonyms:
3-Azetidinol,1-(diphenylmethyl)-;1-(Diphenylmethyl)-3-azetidinol;1-Benzhydrylazetidin-3-ol;1-Benzhydryl-3-hydroxyazetidine;N-(Diphenylmethyl)azetidin-3-ol;1-(Diphenylmethyl)-3-hydroxyazetidine;1-Benzhydryl-3-azetanol;NSC 319045;3-Hydroxy-1-(diphenylmethyl)azetidine;N-(Diphenylmethyl)-3-hydroxyazetidine;N-Benzhydryl-3-azetidinol;N-Benzhydryl-3-hydroxyazetidine
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CAS No:
Characteristics
23.5
2.6
Solid
1.189±0.06 g/cm3(Predicted)
115 °C
353.8±42.0 °C(Predicted)
101.7±22.0 °C
1.641
Room temperature.
1.29E-05mmHg at 25°C
Safety Information
8
36/37/38
26-37/39
Xi,C
Irritant
P260, P264, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P332+P313, P337+P313, P362, P363, P405, P501
H314
|Danger|H314 (88.64%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501|Aggregated GHS information provided by 45 companies from 6 notifications to the ECHA C&L Inventory.
1-Benzhydrylazetidin-3-ol Use and Manufacturing
DIPEA (129 g, 1 mol) was added to a solution of 1-(benzhydrylamino)-3-chloropropan-2-ol (Intermediate 32, 276 g, 1 mol) in ethanol (2 L) at 0°C, then the mixture was refluxed at 90°C overnight. The mixture was then concentrated in vacuo to give the title compound (179 g, 75percent) which could be re-crystallized from acetone and petroleum ether.183 g of diphenylmethylamine and 92.5 g of epichlorohydrin, Add about 400mlIsopropyl alcohol, stir well, Then add 63gSodium carbonate, heated to reflux for 12 hours, and the reaction was complete by HPLC monitoring. filter, Isopropanol washing filter cake, the filtrate recovery isopropyl alcohol, the residue added ethyl acetate dissolved, Add concentrated hydrochloric acid to adjust the pH of 3 to 4, precipitation of large amounts of solid, filter detergent cake. Filter cake added to the water, And then slowly add the liquid alkaline solution, adjust the pH 10 to 11, filter out the solid, Dry to a white solidProduct III 210.9 g, yield 88.2percent, purity 99.98percent.Production Example 191 Example 9(a) Step 1: Step lTo a stirred solution of epichlorohydrin [91] (1 1.3 g, 13.9 mmol) in methanol (50 ml), a-amino- diphenylmethane [92] (25 g, 13.9 mmol) was added dropwise under at room temperature. The resulting solution was refluxed at 70 °C for 72 h. The progress of the reaction was monitored by TLC. After 72 h, the solvent was evaporated under vacuum. The residual solid was washed with 1000 ml of diethyl ether. The resulting residue was purified by column chromatography over 100-200 mesh silica using 2percent MeOH:DCM as eluent to gave l-benzhydrylazetidin-3-ol [93] as a white solid (14.1g, 41percent).ESIMS: 240 (MThe solution of 2-(chloromethyl)oxirane (10 mL, 128 mmol) and PhNaBHA mixture of [(DIPHENYIMETHYL)] amine (2.2 [ML, ] 12.8 mmole), 2-chloromethyloxirane (2.0 [ML, ] 25. 6mmole) in DMF (25 ml) were heated at 95 [°C] for 72 hours. The resultant yellow solution was cooled to [0°] and treated with 0.5 M HCI (250 [ML).] The aqueous layer was washed with methyl [TERT-BUTYL ETHER] (3 x 150 ml), and the organic layers were discarded. The aqueous layer was made basic with [NAOH] and the resultant milky white suspension was extracted with methyl tert-butyl ether (3 x 150 ml). The combined organic layers were washed with brine, dried over [MGS04 AND CONCENTRATED, IN VACUO, ] to a clear oil (3.1 [G).] The oil was triturated with cyclohexane and methyl ter-butyl ether and provided a white solid (2.3 g, 74percent): TLC (4percent methanol-chloroform with 0. 1percent ammonium hydroxide) R, 0.3 [;APOS;H-NMR] [(DMSO-D6, ] 400 MHz) 8 7.40-7. 38 (4H, m), 7.27-7. 23 (4H, m), 7.17-7. 13 (2H, m), 5.28 (1 H, d, J = 6.3 Hz), 4.34 (1H, s), 4.22-4. 18 (1H, m), 3.36-3. 34 (2H, m), 2.69-2. 66 (2H, m).
It is used to identify inhibitors of CYP 3A4.
Computed Properties
Molecular Weight:239.31
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:239.131014166
Monoisotopic Mass:239.131014166
Topological Polar Surface Area:23.5
Heavy Atom Count:18
Complexity:232
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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