(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran

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(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran Basic information
Description Physical Form synthesis
Product Name:(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran
Synonyms:EMpagliflozin int3;Empagliflozin-7;915085-89-5;(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)-benzene;3-[4-[(5-broMo-2-chlorophenyl)Methyl]phenoxy]tetrahydro-;(3S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydro-furan;(3S)-3-[4-[(5-bromo-2-chlorophenyl)methyl]phenoxy]oxolane 915095-89-5;Empagliflozin impurity 10/Empagliflozin 5-Bromo Impurity/(S)-3-[4-(5-Bromo-2-chlorobenzyl)phenoxy]tetrahydrofuran
CAS:915095-89-5
MF:C17H16BrClO2
MW:367.66
EINECS:1592732-453-0
Product Categories:915095-89-5;Empagliflozin Intermediate
Mol File:915095-89-5.mol
(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran Structure
(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran Chemical Properties
Melting point 49-51°C
Boiling point 459.1±45.0 °C(Predicted)
density 1.431±0.06 g/cm3 (20 ºC 760 Torr)
storage temp. Sealed in dry,Room Temperature
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
color White to Off-White
Optical RotationConsistent with structure
InChIInChI=1S/C17H16BrClO2/c18-14-3-6-17(19)13(10-14)9-12-1-4-15(5-2-12)21-16-7-8-20-11-16/h1-6,10,16H,7-9,11H2/t16-/m0/s1
InChIKeyHUNLNKBDQXGMAP-INIZCTEOSA-N
SMILESO1CC[C@H](OC2=CC=C(CC3=CC(Br)=CC=C3Cl)C=C2)C1
Safety Information
HS Code 2932190090
MSDS Information
(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran Usage And Synthesis
Description(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran is used as a reactant to efficiently synthesize SGLT- 2 Epagliflozin inhibitors.
Physical FormSolid
synthesisTo a mixture of AlCl3 (61.7 g, 0.463 mol) and (S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (100 g, 0.231 mol) in toluene (450 mL) was added 1,1,3,3-tetramethyldisiloxane (40.4 g, 0.301 mol) over 1 hour at<20 °C. The mixture was held at 20-23 °C for an additional 1.5 hours and cooled to 0-5 °C. The cooled solution was slowly added to ice-water (400 mL) over 15 min and the layers separated. The organic was treated with 3N NaOH (400 mL) at room temperature for 16-24 hours and the layers were separated. The organic was concentrated to a low volume (~130 mL). After diluted with acetonitrile (450 mL), the solution was again concentrated to a low volume (~130 mL). To the residue was added acetonitrile (400 mL) followed by a slow addition of water (200 mL). The resulting mixture was cooled to 0-3 °C and held for 2 hours. The solids were collected by filtration and dried in oven to give product. (S)-3-(4-(2-chloro-5- bromobenzyl)phenoxy)tetrahydrofuran (2a). 92% as white crystals.
synthesis of (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran
Uses(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran is used as a reactant in the efficient synthesis of empagliflozin inhibitor of SGLT-2 utilizing AlCl3-promoted silane reduction of β-glycopyranoside.
References[1] Organic Letters, 2014, vol. 16, # 16, p. 4090 - 4093
[2] Patent: CN106905305, 2017, A. Location in patent: Paragraph 0056; 00057; 0058; 0059
[3] Patent: US2006/258749, 2006, A1. Location in patent: Page/Page column 24-25
[4] Patent: US2006/258749, 2006, A1. Location in patent: Page/Page column 25
Tag:(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran(915095-89-5) Related Product Information
2,3-Butanediol Empagliflozin (R)-Isomer Empagliflozin Impurity 23 Acetoxy Empagliflozin ((2R,3S,4R,5R,6S)-6-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)Methyl acetate N/A Butanoic acid, 4-chloro-3-hydroxy-, (3S)- (R)-3-(p-toluenesulfonyl) oxytetrahydrofuran Empagliflozin (S)-(+)-3-Hydroxytetrahydrofuran 4-(5-broMo-2-chlorobenzyl)phenol Benzo[b]thiophene, 2-[(5-broMo-2-fluorophenyl)Methyl]- (2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone (2S,3R,4S,5S,6R)-2-(3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)-4-chlorophenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylbromide (S)-3-(4-(2-Chloro-5-iodobenzyl)phenoxy)tetrahydrofuran (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone (S)-3-(4-benzylphenoxy)tetrahydrofuran