(S)-tert-butyl 3-fluoro-2-oxo-3-phenylindoline-1-carboxylate

Base Information

• Chemical Name: (S)-tert-butyl 3-fluoro-2-oxo-3-phenylindoline-1-carboxylate
• CAS No.: 1040749-29-8
• Molecular Formula: C₁₉H₁₈FNO₃
• Molecular Weight: 327.355
• Mol file: 1040749-29-8.mol

Synonyms:(S)-tert-butyl 3-fluoro-2-oxo-3-phenylindoline-1-carboxylate

Chemical Property of (S)-tert-butyl 3-fluoro-2-oxo-3-phenylindoline-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-tert-butyl 3-fluoro-2-oxo-3-phenylindoline-1-carboxylate

There total 6 articles about (S)-tert-butyl 3-fluoro-2-oxo-3-phenylindoline-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: 95.0%

tert-butyl 2-oxo-3-phenylindoline-1-carboxylate (862906-97-6) → (S)-tert-butyl 3-fluoro-2-oxo-3-phenylindoline-1-carboxylate (1040749-29-8)

Guidance literature:

tert-butyl 2-oxo-3-phenylindoline-1-carboxylate; With nickel(II) perchlorate hexahydrate; (1Z,3Z)-1,3-bis{[(S)-4-phenyl-4,5-dihydrooxazol-2-yl]methylene}isoindoline; In diethyl ether; at 20 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

With N-fluorobis(benzenesulfon)imide; In diethyl ether; at 20 ℃; for 6h; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1002/chem.201102375

Reference yield:

tert-butyl 2-oxo-3-phenylindoline-1-carboxylate (862906-97-6) → (R)-tert-butyl 3-fluoro-2-oxo-3-phenylindoline-1-carboxylate (862907-00-4) + (S)-tert-butyl 3-fluoro-2-oxo-3-phenylindoline-1-carboxylate (1040749-29-8)

Guidance literature:

With cesium hydroxide monohydrate; N-fluorobis(benzenesulfon)imide; hydroquinidine (anthraquinone-1,4-diyl) diether; In dichloromethane; acetonitrile; at -80 ℃; for 5h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.200800717

Reference yield:

phenylmagnesium bromide (100-58-3) → (R)-tert-butyl 3-fluoro-2-oxo-3-phenylindoline-1-carboxylate (862907-00-4) + (S)-tert-butyl 3-fluoro-2-oxo-3-phenylindoline-1-carboxylate (1040749-29-8)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / -40 - 20 °C / Inert atmosphere

2: dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere

3: palladium on activated charcoal; hydrogen / methanol / 3 h / 20 °C / Inert atmosphere

4: N-fluorobis(benzenesulfon)imide; silver perchlorate; C₂₈H₃₆Br₂ClFeN₂O₂ / diethyl ether / 3 h / 0 °C / Inert atmosphere; Molecular sieve

With dmap; palladium on activated charcoal; C₂₈H₃₆Br₂ClFeN₂O₂; hydrogen; silver perchlorate; N-fluorobis(benzenesulfon)imide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1039/c4cc01631a

upstream raw materials:

tert-butyl 2-oxo-3-phenylindoline-1-carboxylate

1-(tert-butoxycarbonyl)-2-oxo-3-phenylindolin-3-yl tert-butyl carbonate

1-tert-butoxycarbonylisatin

phenylmagnesium bromide