Benzoic acid (2R,3S,6S,12bS,13S)-3-ethyl-3-hydroxy-12-(toluene-4-sulfonyl)-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-13-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (2R,3S,6S,12bS,13S)-3-ethyl-3-hydroxy-12-(toluene-4-sulfonyl)-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-13-ylmethyl ester
CAS No.:151158-57-5
Molecular Formula:C₃₃H₃₄N₂O₅S
Molecular Weight:570.709
Hs Code.:

Benzoic acid (2R,3S,6S,12bS,13S)-3-ethyl-3-hydroxy-12-(toluene-4-sulfonyl)-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-13-ylmethyl ester

Synonyms:Benzoic acid (2R,3S,6S,12bS,13S)-3-ethyl-3-hydroxy-12-(toluene-4-sulfonyl)-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-13-ylmethyl ester

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Chemical Property of Benzoic acid (2R,3S,6S,12bS,13S)-3-ethyl-3-hydroxy-12-(toluene-4-sulfonyl)-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-13-ylmethyl ester

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Technology Process of Benzoic acid (2R,3S,6S,12bS,13S)-3-ethyl-3-hydroxy-12-(toluene-4-sulfonyl)-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-13-ylmethyl ester

There total 11 articles about Benzoic acid (2R,3S,6S,12bS,13S)-3-ethyl-3-hydroxy-12-(toluene-4-sulfonyl)-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-13-ylmethyl ester 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: 73.0%

: C₄₂H₄₄N₂O₁₀S₂

: 151158-57-5
Benzoic acid (2R,3S,6S,12bS,13S)-3-ethyl-3-hydroxy-12-(toluene-4-sulfonyl)-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-13-ylmethyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethanol; acetic acid;
DOI:10.1016/S0040-4039(00)60609-3

Reference yield:

: C₂₈H₃₂N₂O₄

: 151158-57-5
Benzoic acid (2R,3S,6S,12bS,13S)-3-ethyl-3-hydroxy-12-(toluene-4-sulfonyl)-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-13-ylmethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 100 percent / TsOH / benzene / Heating

2: 97 percent / Et₃N / CH₂Cl₂

3: 76 percent / Pb(OAc)4 / CH₂Cl₂ / -70 deg C to -10 deg C

4: 1) H₂O, AcOH, 2) NaCNBH₃ / 1) THF, 0 deg C

5: 91 percent / pyridine / CH₂Cl₂

6: 96 percent / aq. 80 percent AcOH / Heating

7: 81 percent / n-Bu₄NHSO₄, KOH, H₂O / benzene

8: 82 percent / Et₃N / CH₂Cl₂

9: 45 percent / OsO₄, pyridine / tetrahydrofuran / -10 deg C to 0 deg C

10: 83 percent / NaBH₄ / methanol

11: 100 percent / pyridine

12: 73 percent / H₂ / 10 percent Pd/C / acetic acid; ethanol

With pyridine; lead(IV) acetate; potassium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; water; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; benzene;
DOI:10.1016/S0040-4039(00)60609-3

Reference yield:

: 151158-64-4
C₃₀H₃₆N₂O₅

: 151158-57-5
Benzoic acid (2R,3S,6S,12bS,13S)-3-ethyl-3-hydroxy-12-(toluene-4-sulfonyl)-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-13-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 91 percent / pyridine / CH₂Cl₂

2: 96 percent / aq. 80 percent AcOH / Heating

3: 81 percent / n-Bu₄NHSO₄, KOH, H₂O / benzene

4: 82 percent / Et₃N / CH₂Cl₂

5: 45 percent / OsO₄, pyridine / tetrahydrofuran / -10 deg C to 0 deg C

6: 83 percent / NaBH₄ / methanol

7: 100 percent / pyridine

8: 73 percent / H₂ / 10 percent Pd/C / acetic acid; ethanol

With pyridine; potassium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; water; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; benzene;
DOI:10.1016/S0040-4039(00)60609-3