(2'S,3R,4'R)-ethyl 1-benzyl-4'-hydroxy-2-oxo-4',5'-dihydro-2'H-spiro[indoline-3,3'-thiophene]-2'-carboxylate

Base Information

Chemical Name:(2'S,3R,4'R)-ethyl 1-benzyl-4'-hydroxy-2-oxo-4',5'-dihydro-2'H-spiro[indoline-3,3'-thiophene]-2'-carboxylate
CAS No.:1376632-17-5
Molecular Formula:C₂₁H₂₁NO₄S
Molecular Weight:383.468
Hs Code.:

Synonyms:(2'S,3R,4'R)-ethyl 1-benzyl-4'-hydroxy-2-oxo-4',5'-dihydro-2'H-spiro[indoline-3,3'-thiophene]-2'-carboxylate

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Chemical Property of (2'S,3R,4'R)-ethyl 1-benzyl-4'-hydroxy-2-oxo-4',5'-dihydro-2'H-spiro[indoline-3,3'-thiophene]-2'-carboxylate

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Technology Process of (2'S,3R,4'R)-ethyl 1-benzyl-4'-hydroxy-2-oxo-4',5'-dihydro-2'H-spiro[indoline-3,3'-thiophene]-2'-carboxylate

There total 3 articles about (2'S,3R,4'R)-ethyl 1-benzyl-4'-hydroxy-2-oxo-4',5'-dihydro-2'H-spiro[indoline-3,3'-thiophene]-2'-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: 88.0%

: 40018-26-6
1,4-dithiane-2,5-diol

: 411237-64-4
ethyl 2-(1-benzyl-2-oxoindolin-3-ylidene)acetate

: 1376632-17-5
(2'S,3R,4'R)-ethyl 1-benzyl-4'-hydroxy-2-oxo-4',5'-dihydro-2'H-spiro[indoline-3,3'-thiophene]-2'-carboxylate

Guidance literature:: ethyl 2-(1-benzyl-2-oxoindolin-3-ylidene)acetate; With nickel(II) triflate; C₃₉H₆₀N₄O₄; In dichloromethane; at 35 ℃; Inert atmosphere;

1,4-dithiane-2,5-diol; In dichloromethane; at 35 ℃; for 2h; stereoselective reaction; Inert atmosphere;
DOI:10.1002/adsc.201400964

Reference yield:

: 40018-26-6
1,4-dithiane-2,5-diol

: 13672-24-7
ethyl (2E)-(1-benzyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)acetate

: 1376632-17-5
(2'S,3R,4'R)-ethyl 1-benzyl-4'-hydroxy-2-oxo-4',5'-dihydro-2'H-spiro[indoline-3,3'-thiophene]-2'-carboxylate

: 1376632-20-0
(2'R,3S,4'S)-ethyl 1-benzyl-4'-hydroxy-2-oxo-4',5'-dihydro-2'H-spiro[indoline-3,3'-thiophene]-2'-carboxylate

Guidance literature:: ethyl (2E)-(1-benzyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)acetate; With C₃₁H₂₆F₆N₄O₂; magnesium sulfate; In dichloromethane; at 15 ℃; for 0.5h;

1,4-dithiane-2,5-diol; In dichloromethane; for 6h; optical yield given as %ee; diastereoselective reaction;
DOI:10.1039/c2cc30931a

Reference yield:

: 1217-89-6
1-benzylisatin

: 1376632-17-5
(2'S,3R,4'R)-ethyl 1-benzyl-4'-hydroxy-2-oxo-4',5'-dihydro-2'H-spiro[indoline-3,3'-thiophene]-2'-carboxylate

: 1376632-20-0
(2'R,3S,4'S)-ethyl 1-benzyl-4'-hydroxy-2-oxo-4',5'-dihydro-2'H-spiro[indoline-3,3'-thiophene]-2'-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 0 °C

2.1: 3-(3,5-bis-trifluoromethyl-phenylamino)-4-{[(S)-(6-methoxy-quinolin-4-yl)-((R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-amino}-cyclobut-3-ene-1,2-dione; magnesium sulfate / dichloromethane / 0.5 h / 15 °C

2.2: 11 h

With 3-(3,5-bis-trifluoromethyl-phenylamino)-4-{[(S)-(6-methoxy-quinolin-4-yl)-((R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-amino}-cyclobut-3-ene-1,2-dione; magnesium sulfate; In tetrahydrofuran; dichloromethane;
DOI:10.1039/c2cc30931a