(S)-(-)-1'-benzyl-1',2'-dihydro-2'-oxospiro[1,4-dioxaspiro[4.5]dec-6-ene8,3'-3'H-indole]

Base Information

Chemical Name:(S)-(-)-1'-benzyl-1',2'-dihydro-2'-oxospiro[1,4-dioxaspiro[4.5]dec-6-ene8,3'-3'H-indole]
CAS No.:142613-66-9
Molecular Formula:C₂₂H₂₁NO₃
Molecular Weight:347.414
Hs Code.:

Synonyms:(S)-(-)-1'-benzyl-1',2'-dihydro-2'-oxospiro[1,4-dioxaspiro[4.5]dec-6-ene8,3'-3'H-indole]

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Chemical Property of (S)-(-)-1'-benzyl-1',2'-dihydro-2'-oxospiro[1,4-dioxaspiro[4.5]dec-6-ene8,3'-3'H-indole]

Chemical Property:

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Technology Process of (S)-(-)-1'-benzyl-1',2'-dihydro-2'-oxospiro[1,4-dioxaspiro[4.5]dec-6-ene8,3'-3'H-indole]

There total 12 articles about (S)-(-)-1'-benzyl-1',2'-dihydro-2'-oxospiro[1,4-dioxaspiro[4.5]dec-6-ene8,3'-3'H-indole] 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:

: 142613-79-4
1,4-Dioxa-spiro[4.5]dec-7-ene-8-carboxylic acid benzyl-(2-iodo-phenyl)-amide

: 142613-66-9
(S)-(-)-1'-benzyl-1',2'-dihydro-2'-oxospiro[1,4-dioxaspiro[4.5]dec-6-ene8,3'-3'H-indole]

: 142613-67-0
(R)-(+)-1'-benzyl-1',2'-dihydro-2'-oxospiro[1,4-dioxaspiro[4.5]dec-6-ene-8,3'-3'H-indole]

Guidance literature:: With 1,2,2,6,6-pentamethylpiperidine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In N,N-dimethyl acetamide; at 80 - 100 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1021/jo00043a005

Reference yield:

: 615-43-0
2-iodophenylamine

: 142613-66-9
(S)-(-)-1'-benzyl-1',2'-dihydro-2'-oxospiro[1,4-dioxaspiro[4.5]dec-6-ene8,3'-3'H-indole]

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N / tetrahydrofuran / 5 h / Heating

2: 44 percent / NaH

3: Pd₂(dba)3, (R)-BINAP, 1,2,2,6,6-pentamethylpiperidine / N,N-dimethyl-acetamide / 6.5 h / 100 °C

4: TBAF

5: 1.) NaH / 1.) THF

With 1,2,2,6,6-pentamethylpiperidine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; tetrabutyl ammonium fluoride; sodium hydride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triethylamine; In tetrahydrofuran; N,N-dimethyl acetamide;
DOI:10.1021/ja980786p

Reference yield:

: 72445-22-8
1,4-dioxaspiro[4.5]dec-7-ene-8-carbaldehyde

: 142613-66-9
(S)-(-)-1'-benzyl-1',2'-dihydro-2'-oxospiro[1,4-dioxaspiro[4.5]dec-6-ene8,3'-3'H-indole]

Guidance literature:: Multi-step reaction with 7 steps

1: 81 percent / aq. NaClO₂, NaH₂PO₄, 2,3-dimethyl-2-butene / 2-methyl-propan-2-ol / 24 h / Ambient temperature

2: 1.) NaH, 2.) SOCl₂ / 1.) THF, RT, 2 h, 2.) THF, RT, 2.5 h

3: Et₃N / tetrahydrofuran / 5 h / Heating

4: 44 percent / NaH

5: Pd₂(dba)3, (R)-BINAP, 1,2,2,6,6-pentamethylpiperidine / N,N-dimethyl-acetamide / 6.5 h / 100 °C

6: TBAF

7: 1.) NaH / 1.) THF

With 1,2,2,6,6-pentamethylpiperidine; sodium chlorite; sodium dihydrogenphosphate; thionyl chloride; 2,3-Dimethyl-2-butene; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; tetrabutyl ammonium fluoride; sodium hydride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triethylamine; In tetrahydrofuran; N,N-dimethyl acetamide; tert-butyl alcohol;
DOI:10.1021/ja980786p