(Z)-methyl 8,9-dihydro-7-hydroxy-8-(2-(tert-butyldiphenylsilyloxymethyl)allyl)-2,9,9-trimethyl-2H-cyclohepta[cd]indole-6-carboxylate

Base Information

Chemical Name:(Z)-methyl 8,9-dihydro-7-hydroxy-8-(2-(tert-butyldiphenylsilyloxymethyl)allyl)-2,9,9-trimethyl-2H-cyclohepta[cd]indole-6-carboxylate
CAS No.:1228023-16-2
Molecular Formula:C₃₇H₄₃NO₄Si
Molecular Weight:593.838
Hs Code.:

Synonyms:(Z)-methyl 8,9-dihydro-7-hydroxy-8-(2-(tert-butyldiphenylsilyloxymethyl)allyl)-2,9,9-trimethyl-2H-cyclohepta[cd]indole-6-carboxylate

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Chemical Property of (Z)-methyl 8,9-dihydro-7-hydroxy-8-(2-(tert-butyldiphenylsilyloxymethyl)allyl)-2,9,9-trimethyl-2H-cyclohepta[cd]indole-6-carboxylate

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Technology Process of (Z)-methyl 8,9-dihydro-7-hydroxy-8-(2-(tert-butyldiphenylsilyloxymethyl)allyl)-2,9,9-trimethyl-2H-cyclohepta[cd]indole-6-carboxylate

There total 11 articles about (Z)-methyl 8,9-dihydro-7-hydroxy-8-(2-(tert-butyldiphenylsilyloxymethyl)allyl)-2,9,9-trimethyl-2H-cyclohepta[cd]indole-6-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: 77.0%

: 1228023-20-8
3-oxo-4-[1',1'-dimethyl-1'-(4-bromo-1-methylindol-3-yl)-methyl]-6-methylene-7-(tert-butyldiphenylsilyloxy)-heptanoate methyl ester

: 1228023-16-2
(Z)-methyl 8,9-dihydro-7-hydroxy-8-(2-(tert-butyldiphenylsilyloxymethyl)allyl)-2,9,9-trimethyl-2H-cyclohepta[cd]indole-6-carboxylate

Guidance literature:: With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; at 150 ℃; for 0.0833333h; Microwave irradiation;
DOI:10.1021/ol1006373

Reference yield:

: 913253-34-6
{[2-(bromomethyl)prop-2-en-1-yl]oxy}(tert-butyl)diphenylsilane

: 1228023-16-2
(Z)-methyl 8,9-dihydro-7-hydroxy-8-(2-(tert-butyldiphenylsilyloxymethyl)allyl)-2,9,9-trimethyl-2H-cyclohepta[cd]indole-6-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.83 h / 0 °C / Inert atmosphere

1.2: 3.92 h / -78 - 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / acetone / 22 h

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

3.2: 0.83 h / Inert atmosphere

4.1: trimethylsilyl trifluoromethanesulfonate / toluene / 0.03 h / -78 °C

4.2: 19.5 h / -78 - 20 °C

5.1: toluene / 21 h / 100 °C

6.1: sodium t-butanolate; palladium diacetate; tri-tert-butyl phosphine / toluene / 0.08 h / 150 °C / 1034.32 Torr / Inert atmosphere; Microwave irradiation

With n-butyllithium; tri-tert-butyl phosphine; trimethylsilyl trifluoromethanesulfonate; palladium diacetate; sodium hexamethyldisilazane; diisopropylamine; trifluoroacetic acid; sodium t-butanolate; In tetrahydrofuran; hexane; acetone; toluene;
DOI:10.1016/j.tet.2013.03.010

Reference yield:

: 1228023-15-1
O-(tert-butyldiphenylsilyl)-2-methylene-4-(2,2-dimethyl-4H-1,3-dioxin-4-one-6-yl)-5-(4-bromo-1-methylindol-3-yl)-5-methyl-hexan-1-ol

: 1228023-16-2
(Z)-methyl 8,9-dihydro-7-hydroxy-8-(2-(tert-butyldiphenylsilyloxymethyl)allyl)-2,9,9-trimethyl-2H-cyclohepta[cd]indole-6-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: toluene / 21 h / 100 °C

2: sodium t-butanolate; palladium diacetate; tri-tert-butyl phosphine / toluene / 0.08 h / 150 °C / 1034.32 Torr / Inert atmosphere; Microwave irradiation

With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene;
DOI:10.1016/j.tet.2013.03.010