(+)-(1S,7aS)-4-(2-bromo-5-methoxy-benzyl)-1-tert-butoxy-7a-methyl-2,3,7,7a-tetrahydro-1H-indene

Base Information

Chemical Name:(+)-(1S,7aS)-4-(2-bromo-5-methoxy-benzyl)-1-tert-butoxy-7a-methyl-2,3,7,7a-tetrahydro-1H-indene
CAS No.:656824-47-4
Molecular Formula:C₂₂H₂₉BrO₂
Molecular Weight:405.375
Hs Code.:

Synonyms:(+)-(1S,7aS)-4-(2-bromo-5-methoxy-benzyl)-1-tert-butoxy-7a-methyl-2,3,7,7a-tetrahydro-1H-indene

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Chemical Property of (+)-(1S,7aS)-4-(2-bromo-5-methoxy-benzyl)-1-tert-butoxy-7a-methyl-2,3,7,7a-tetrahydro-1H-indene

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Technology Process of (+)-(1S,7aS)-4-(2-bromo-5-methoxy-benzyl)-1-tert-butoxy-7a-methyl-2,3,7,7a-tetrahydro-1H-indene

There total 6 articles about (+)-(1S,7aS)-4-(2-bromo-5-methoxy-benzyl)-1-tert-butoxy-7a-methyl-2,3,7,7a-tetrahydro-1H-indene 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: 72.0%

: 66192-25-4
2-bromo-5-methoxybenzyl chloride

: 656824-48-5
(+)-2-((1S,7aS)-1-tert-butoxy-7a-methyl-2,3,7,7a-tetrahydro-1H-inden-4-yl)-5,5-dimethyl-[1,3,2]dioxaborinane

: 656824-47-4
(+)-(1S,7aS)-4-(2-bromo-5-methoxy-benzyl)-1-tert-butoxy-7a-methyl-2,3,7,7a-tetrahydro-1H-indene

Guidance literature:: With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 22h; Heating;
DOI:10.1016/S0022-328X(03)00720-4

Reference yield:

: 41878-38-0
(1S,7aS)-1-tert-butoxy-7a-methyl-1,2,3,6,7,7a-hexahydro-5H-inden-5-one

: 656824-47-4
(+)-(1S,7aS)-4-(2-bromo-5-methoxy-benzyl)-1-tert-butoxy-7a-methyl-2,3,7,7a-tetrahydro-1H-indene

Guidance literature:: Multi-step reaction with 6 steps

1.1: 80 percent / Br / diethyl ether; acetic acid; 2,4,6-trimethyl-pyridine / 24 h / 20 °C

2.1: 80 percent / NaBH₄; CeCl₃*7H₂O / methanol / 4 h / 0 - 20 °C

3.1: 96 percent / n-Bu₄NHSO₄ / aq. NaOH / 18 h / 20 °C

4.1: 55 percent / bis-(2-methoxy-ethyl) ether / 200 °C / microwave irradiation

5.1: tBuLi; TMEDA / tetrahydrofuran; pentane / 0.5 h / -78 °C

5.2: B(Oi-Pr)3 / tetrahydrofuran; pentane / 18 h / -78 - 20 °C

5.3: 77 percent / toluene / 22 h / 20 °C

6.1: 72 percent / NaOH / Pd(PPh₃)4 / tetrahydrofuran / 22 h / Heating

With sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; N,N,N,N,-tetramethylethylenediamine; bromine; tert.-butyl lithium; tetra(n-butyl)ammonium hydrogensulfate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 2,4,6-trimethyl-pyridine; methanol; sodium hydroxide; diethyl ether; diethylene glycol dimethyl ether; acetic acid; pentane; 6.1: Suzuki coupling;
DOI:10.1016/S0022-328X(03)00720-4

Reference yield:

: 656824-52-1
(+)-(1S,7aS)-4-bromo-1-tert-butoxy-7a-methyl-2,3,7,7a-tetrahydro-1H-indene

: 656824-47-4
(+)-(1S,7aS)-4-(2-bromo-5-methoxy-benzyl)-1-tert-butoxy-7a-methyl-2,3,7,7a-tetrahydro-1H-indene

Guidance literature:: Multi-step reaction with 2 steps

1.1: tBuLi; TMEDA / tetrahydrofuran; pentane / 0.5 h / -78 °C

1.2: B(Oi-Pr)3 / tetrahydrofuran; pentane / 18 h / -78 - 20 °C

1.3: 77 percent / toluene / 22 h / 20 °C

2.1: 72 percent / NaOH / Pd(PPh₃)4 / tetrahydrofuran / 22 h / Heating

With sodium hydroxide; N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pentane; 2.1: Suzuki coupling;
DOI:10.1016/S0022-328X(03)00720-4