tert-Butyl indoline-1-carboxylate

Base Information

• Chemical Name: tert-Butyl indoline-1-carboxylate
• CAS No.: 143262-10-6
• Molecular Formula: C13H17 N O2
• Molecular Weight: 219.283
• Hs Code.: 2933990090
• European Community (EC) Number: 623-971-8
• DSSTox Substance ID: DTXSID30394808
• Nikkaji Number: J914.702K
• Wikidata: Q82194435
• Mol file: 143262-10-6.mol

Synonyms:tert-Butyl indoline-1-carboxylate;143262-10-6;1-BOC-INDOLINE;Tert-butyl 2,3-dihydroindole-1-carboxylate;1H-Indole-1-carboxylic acid, 2,3-dihydro-, 1,1-dimethylethyl ester;2,3-dihydroindole-1-carboxylic acid tert-butyl ester;tert-butyl 1-indolinecarboxylate;1-t-butyloxycarbonylindoline;N-(t-butoxycarbonyl)indoline;SCHEMBL552069;1-(tert-butoxycarbonyl)indoline;tert-Butylindoline-1-carboxylate;GWAXLDLPPZPQLO-UHFFFAOYSA-;DTXSID30394808;GWAXLDLPPZPQLO-UHFFFAOYSA-N;MFCD01318399;AKOS009158345;SB64104;tert-Butyl indoline-1-carboxylate, 98%;tert-Butyl?3-oxopyrrolidine-1-carboxylate;CS-0082136;FT-0607418;EN300-127043;F17563;tert-butyl 2,3-dihydro-1H-indole-1-carboxylate;A808047;A838402;J-007784;1,1-dimethylethyl 2,3-dihydro-1H-indole-1-carboxylate;2,3-dihydro-1H-indole-1-carboxylic acid tert-butyl ester;InChI=1/C13H17NO2/c1-13(2,3)16-12(15)14-9-8-10-6-4-5-7-11(10)14/h4-7H,8-9H2,1-3H3

Chemical Property of tert-Butyl indoline-1-carboxylate

Chemical Property:

• Vapor Pressure: 0.000869mmHg at 25°C
• Melting Point: 46-50 °C(lit.)
• Refractive Index: 1.544
• Boiling Point: 83-84 °C0.1 mm Hg(lit.)
• Flash Point: 138°C
• PSA: 29.54000
• Density: 1.114g/cm³
• LogP: 3.04920
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 219.125928785
• Heavy Atom Count: 16
• Complexity: 270

Purity/Quality:

97% ^*data from raw suppliers

1-Boc-Indoline ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC2=CC=CC=C21
• Uses: Reactant in preparation of aryl alkyl amines via alkylation reactions catalyzed by Pd 1 Reactant in preparation of allyl- and arylindolines 2 Reactant in modular indole synthesis of the highly strained CDEF parent tetracycle of nodulisporic acids A and B 3 Reactant in asymmetric synthesis of β-amino esters via rhodium prolinate complex-catalyzed α-C-H activation / carbenoid insertion reactions 4 Reactant in preparation of substituted indolines and tetrahydroquinolines via cycloaddition approach. Reactant in preparation of aryl alkyl amines via alkylation reactions catalyzed by PdReactant in preparation of allyl- and arylindolinesReactant in modular indole synthesis of the highly strained CDEF parent tetracycle of nodulisporic acids A and BReactant in asymmetric synthesis of β-amino esters via rhodium prolinate complex-catalyzed α-C-H activation / carbenoid insertion reactionsReactant in preparation of substituted indolines and tetrahydroquinolines via cycloaddition approach

Technology Process of tert-Butyl indoline-1-carboxylate

There total 7 articles about tert-Butyl indoline-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

4-methyl-1H-imidazole (822-36-6) + 2-(mesyloxy)-1-[2-[(tert-butoxycarbonyl)amino]phenyl]ethane (193806-50-7) → 2-(5-methyl-1H-imidazol-1-yl)-1-[2-[(tert-butoxycarbonyl)-amino]phenyl]ethane (892393-34-9) + 2-(4-methyl-1H-imidazol-1-yl)-1-[2-[(tert-butoxycarbonyl)-amino]phenyl]ethane (892393-33-8) + 1-(tert-butoxycarbonyl)indoline (143262-10-6)

Guidance literature:

4-methyl-1H-imidazole; With sodium hydride; In N,N-dimethyl-formamide; at 25 ℃; for 0.5h;

2-(mesyloxy)-1-[2-[(tert-butoxycarbonyl)amino]phenyl]ethane; In N,N-dimethyl-formamide; at 25 ℃; for 2.5h; Product distribution / selectivity;

Reference yield: 58.0%

1,3-dioxoisoindolin-2-yl 3-((tert-butoxycarbonyl)(phenyl)amino)propanoate → tertbutylethyl(phenyl)carbamate (210285-26-0) + indole-1-carboxylic acid tert-butyl ester (75400-67-8) + 1-(tert-butoxycarbonyl)indoline (143262-10-6)

Guidance literature:

With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; trifluoroacetic acid; In dimethyl sulfoxide; at 20 ℃; for 0.583333h; Irradiation;

DOI:10.1021/acs.joc.9b00432

Reference yield: 45.0%

1-indoline (496-15-1) + 2-acetyl-1-<(1,1-dimethylethoxy)carbonyl>pyrrole (75400-61-2) → indole (120-72-9) + N-(1-(thiophen-2-yl)ethyl)-1H-indole + 1-(tert-butoxycarbonyl)indoline (143262-10-6)

Guidance literature:

With bismuth (III) nitrate pentahydrate; In acetonitrile; at 120 ℃; for 6h; Sealed tube;

DOI:10.1002/jhet.2457

upstream raw materials:

benzophenone

tert-butyl 5-bromoindoline-1-carboxylate

N,N-dimethyl-formamide

4-methyl-1H-imidazole

Downstream raw materials:

5,6-dihydro-1-(p-methoxyphenyl)-1H,3H-pyrrolo<3,2,1-ij>-3,1-benzoxazin-3-one

tert-butyl 7-bromoindoline-1-carboxylate

indoline-7-carboxyaldehyde

1-(tert-Butoxycarbonyl)-7-<(4-methylphenyl)sulfonyl>indoline