(R)-5-fluoro-1-methyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2,6'(1H,3'H)-dione

Base Information

Chemical Name:(R)-5-fluoro-1-methyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2,6'(1H,3'H)-dione
CAS No.:1332645-62-1
Molecular Formula:C₂₀H₁₆FNO₄
Molecular Weight:353.35
Hs Code.:

Synonyms:(R)-5-fluoro-1-methyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2,6'(1H,3'H)-dione

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Chemical Property of (R)-5-fluoro-1-methyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2,6'(1H,3'H)-dione

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Technology Process of (R)-5-fluoro-1-methyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2,6'(1H,3'H)-dione

There total 5 articles about (R)-5-fluoro-1-methyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2,6'(1H,3'H)-dione 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: 80.0%

: 773-91-1
5-fluoro-1-methylisatin

: (E)-3-(4-methoxyphenyl)but-2-enoyl chloride

: 1332645-62-1
(R)-5-fluoro-1-methyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2,6'(1H,3'H)-dione

Guidance literature:: With BF₄*C₃₃H₄₂N₃OSi⁽¹⁺⁾; caesium carbonate; triethylamine; In tetrahydrofuran; at -40 - 20 ℃; for 20h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1002/adsc.201100178

Reference yield:

: 773-91-1
5-fluoro-1-methylisatin

: 103987-50-4
3-(4-methoxyphenyl)-2-buten-1-al

: 1332645-62-1
(R)-5-fluoro-1-methyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2,6'(1H,3'H)-dione

: (S)-5-fluoro-4'-(4-methoxyphenyl)-1-methylspiro[indoline-3,2'-pyran]-2,6'(3'H)-dione

Guidance literature:: With (S)-5-benzyl-2-mesityl-6,6-dimethyl-5,6-dihydro-8H-[1,2,4]triazolo[3,4-c][1,4]oxazin-2-ium tetrafluoroborate; 3,3′,5,5′-tetra-tert-butyl[1,1′-bi(cyclohexylidene)]-2,2′,5,5′-tetraen-4-one; caesium carbonate; In tetrahydrofuran; at 20 ℃; for 12h; Overall yield = 59 %; enantioselective reaction; Inert atmosphere; Sealed tube;
DOI:10.1021/acscombsci.5b00197

Reference yield:

: 19169-94-9
(E)-3-(4-methoxyphenyl)-2-butenoic acid

: 1332645-62-1
(R)-5-fluoro-1-methyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2,6'(1H,3'H)-dione

Guidance literature:: Multi-step reaction with 2 steps

1: oxalyl dichloride; N,N-dimethyl-formamide / 5 h / 0 - 20 °C / Inert atmosphere

2: BF₄*C₃₃H₄₂N₃OSi⁽¹⁺⁾; caesium carbonate; triethylamine / tetrahydrofuran / 20 h / -40 - 20 °C / Inert atmosphere

With oxalyl dichloride; BF₄*C₃₃H₄₂N₃OSi⁽¹⁺⁾; caesium carbonate; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran;
DOI:10.1002/adsc.201100178