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Chemistry
Heterocyclic Building Blocks
Indolines
Methyl 2-benzylisoindoline-5-carboxylate
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[ CAS No. 127168-94-9 ] {[proInfo.proName]}

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Chemical Structure| 127168-94-9
Chemical Structure| 127168-94-9
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CAS No. :127168-94-9 MDL No. :MFCD16621700
Formula : C17H17NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 267.32 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 127168-94-9 ]

* 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 [ 127168-94-9 ]

[ 127168-94-9 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 38404-42-1 ]
  • [ 127168-94-9 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2647 - 2652
[2]Patent: WO2022/3610,2022,A1
  • 2
  • [ 127168-94-9 ]
  • [ 691-64-5 ]
  • [ 368441-44-5 ]
YieldReaction ConditionsOperation in experiment
With poly(methylhydrosiloxane) In ethanol at 20℃; 12 Description 12; N-T-BUTOXYCARBONYL-5-METHOXYCARBONYLISOINDOLINE (D12) A mixture of di t-butyidicarbonate (0.9g) and N-benzyl-5-methoxycarbonylisoindoline (D11) (200mg) in ETOH (10ML) at rt was treated with poly (methylhydrosiloxane) (0. 67ml) and palladium hydroxide on carbon (50mg, 20% Pd) and stirred overnight. The mixture was filtered and evaporated. The residue was chromatographed on a silica gel flash column [step gradient 5-20% EtOAc in light petroleum 40-60] to give the title compound (D12) (0.64g). MS electrospray (+ion) 278 (MH+). 1H NMR #(CDCL3) : 7.94 (2H, m), 7.32 (1 H, m), 4.72 (2H, s), 4.68 (2H, s), 3.92 (3H, s), 1.52 (9H, s).
Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2004/37788, 2004, A1 Location in patent: Page 15
  • 3
  • [ 38404-42-1 ]
  • [ 100-46-9 ]
  • [ 127168-94-9 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; sodium bicarbonate; (E)-3,3'-(diazene-1,2-diyl)bis(2-methylpropanenitrile); triethylamine; In tetrachloromethane; toluene; a) Methyl 2,3-dihydro-2-(phenylmethyl)-1H-isoindole-5-carboxylate A mixture of 77.0 g (0.469 Mol) of <strong>[38404-42-1]methyl 3,4-dimethylbenzoate</strong>, 178.0 g (1.0 Mol) of N-bromosuccinimide, 0.5 g of azoisobutyronitrile and 800 ml of tetrachloromethane was refluxed for 1 hour whilst simultaneously being subjected to intensive illumination with a 1000-Watt daylight bulb. The mixture was allowed to cool to about 40C, then filtered and the filter residue was washed thoroughly with 200 ml of tetrachloromethane. Within about 30 minutes, at a reaction temperature of +30C, a mixture of 53.6 g (0.575 Mol) of benzenemethanamine, 101.2 g (1.0 Mol) of triethylamine and 150 ml of toluene was added to the combined filtrates. The resulting mixture was refluxed for 3 hours, then left overnight at ambient temperature and filtered to remove the precipitate formed. The filtrate was freed from the solvent in vacuo , the residue remaining was distributed between tert.butyl-methylether and 20% aqueous citric acid, then the aqueous phase was extracted thoroughly with tert.butyl-methylether and ethyl acetate. Batches of sodium hydrogen carbonate were added to the aqueous phase until the development of carbon dioxide ceased, then the mixture was exhaustively extracted with a tert.butyl-methylether/ethyl acetate mixture (1:1 v/v). The combined extracts were worked up in the usual way and yielded 48.1 g (38% of theory) of colourless crystals, Mp. 72C. IR (CH2Cl2): 1735 (Carboxylate-C=O) cm-1
With N-Bromosuccinimide; sodium bicarbonate; (E)-3,3'-(diazene-1,2-diyl)bis(2-methylpropanenitrile); triethylamine; In tetrachloromethane; toluene; a Methyl 2,3-dihydro-2-(phenylmethyl)-1H-isoindole-5-carboxylate A mixture of 77.0 g (0.469 Mol) of <strong>[38404-42-1]methyl 3,4-dimethylbenzoate</strong>, 178.0 g (1.0 Mol) of N-bromosuccinimide, 0.5 g of azoisobutyronitrile and 800 ml of tetrachloromethane was refluxed for 1 hour whilst simultaneously being subjected to intensive illumination with a 1000-Watt daylight bulb. The mixture was allowed to cool to about 40 C., then filtered and the filter residue was washed thoroughly with 200 ml of tetrachloromethane. Within about 30 minutes, at a reaction temperature of +30 C., a mixture of 53.6 g (0.575 Mol) of benzenemethanamine, 101.2 g (1.0 Mol) of triethylamine and 150 ml of toluene was added to the combined filtrates. The resulting mixture was refluxed for 3 hours, then left overnight at ambient temperature and filtered to remove the precipitate formed. The filtrate was freed from the solvent in vacuo, the residue remaining was distributed between tert.butyl-methyl-ether and 20% aqueous citric acid, then the aqueous phase was extracted thoroughly with tert.butyl-methylether and ethyl acetate. Batches of sodium hydrogen carbonate were added to the aqueous phase until the development of carbon dioxide ceased, then the mixture was exhaustively extracted with a tert.butyl-methylether/ethyl acetate mixture (1:1 v/v). The combined extracts were worked up in the usual way and yielded 48.1 g (38% of theory) of colourless crystals, Mp. 72 C. IR (CH2 Cl2): 1735 (Carboxylate-C=O) cm-1
Reference： [1]Patent: EP885186,2003,B1
[2]Patent: US6114390,2000,A
  • 4
  • [ 56-23-5 ]
  • [ 38404-42-1 ]
  • [ 127168-94-9 ]
  • [ 20896-23-5 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; dibenzoyl peroxide; (2) 18.1 g of <strong>[38404-42-1]methyl 3,4-dimethylbenzoate</strong>, 39.2 g of N-bromosuccinimide, 200 mg of benzoyl peroxide, and 200 ml of carbontetrachloride were processed in a similar manner as in Reference Example 6-(1) to give a mixture containing methyl 3,4-bis-(bromomethyl)benzoate as a major component. (3) The procedure of Reference Example 14-(3) was followed using the whole mixture prepared above, 11.8 g of benzylamine, and 22.9 g of triethylamine to give 16.0 g of 2-benzyl-5-methoxycarbonylisoindoline.
Reference： [1]Patent: US5026856,1991,A
  • 5
  • [ 127168-94-9 ]
  • [ 149353-71-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: poly(methylhydrosiloxane) / palladium(II) hydroxide/carbon / ethanol / 20 °C 2: sodium hydroxide / methanol; water / 1 h / 60 °C
Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2004/37788, 2004, A1
  • 6
  • [ 127168-94-9 ]
  • [ 127168-93-8 ]
YieldReaction ConditionsOperation in experiment
88% With hydrogenchloride; palladium on activated charcoal; hydrogen In methanol at 25℃; for 6h; 4 Step-4: Synthesis of Methyl isoindoline-5-carboxylate: To a stirred solution of methyl 2-benzylisoindoline-5-carboxylate (8.70 g, 32.5 mmol) and methanol (400 mL), Pd/C (2.77 g, 26.0 mmol) was added followed by slow addition of cone hydrochloric acid (8.70 mL, 286 mmol). The reaction mixture was stirred under hydrogen gas atmosphere for 6 h at 25 °C. The reaction mixture was filtered through a celite bed, and the filtrate was evaporated at reduced pressure to obtain a crude material. This was triturated in acetonitrile, the obtained suspension was filtered, and the solid obtained was dried at reduced pressure to afford the hydrochloride salt of methyl isoindoline-5- carboxylate (5.1 g, 28.8 mmol, 88 % yield). M/Z [M+H]: 177.95; -NMR (400 MHz, DMSO-r 6) d 9.99 (bs, 2H), 8.00 (s, 1H), 7.94 (dd, J = 7.8, 1.5 Hz, 1H), 7.54 (d, J = 8.1 Hz, 1H), 4.55 (d, J = 5.1 Hz, 4H), 3.86 (s, 3H).
88% With hydrogenchloride; palladium on activated charcoal; hydrogen In methanol at 25℃; for 6h; 4 Step-4: Synthesis of Methyl isoindoline-5-carboxylate: To a stirred solution of methyl 2-benzylisoindoline-5-carboxylate (8.70 g, 32.5 mmol) and methanol (400 mL), Pd/C (2.77 g, 26.0 mmol) was added followed by slow addition of cone hydrochloric acid (8.70 mL, 286 mmol). The reaction mixture was stirred under hydrogen gas atmosphere for 6 h at 25 °C. The reaction mixture was filtered through a celite bed, and the filtrate was evaporated at reduced pressure to obtain a crude material. This was triturated in acetonitrile, the obtained suspension was filtered, and the solid obtained was dried at reduced pressure to afford the hydrochloride salt of methyl isoindoline-5- carboxylate (5.1 g, 28.8 mmol, 88 % yield). M/Z [M+H]: 177.95; -NMR (400 MHz, DMSO-r 6) d 9.99 (bs, 2H), 8.00 (s, 1H), 7.94 (dd, J = 7.8, 1.5 Hz, 1H), 7.54 (d, J = 8.1 Hz, 1H), 4.55 (d, J = 5.1 Hz, 4H), 3.86 (s, 3H).
Reference： [1]Current Patent Assignee: PI INDUSTRIES LTD - WO2022/3610, 2022, A1 Location in patent: Page/Page column 79
[2]Current Patent Assignee: PI INDUSTRIES LTD - WO2022/3610, 2022, A1 Location in patent: Page/Page column 79

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