(1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-<(dimethylphenylsilyl)methyl>hexahydrocyclopentapyrrole

Base Information

Chemical Name:(1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-<(dimethylphenylsilyl)methyl>hexahydrocyclopentapyrrole
CAS No.:237404-25-0
Molecular Formula:C₂₃H₃₁NO₂SSi
Molecular Weight:413.656
Hs Code.:

(1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-<(dimethylphenylsilyl)methyl>hexahydrocyclopenta<c>pyrrole

Synonyms:(1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-<(dimethylphenylsilyl)methyl>hexahydrocyclopentapyrrole

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Chemical Property of (1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-<(dimethylphenylsilyl)methyl>hexahydrocyclopentapyrrole

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Technology Process of (1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-<(dimethylphenylsilyl)methyl>hexahydrocyclopentapyrrole

There total 5 articles about (1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-<(dimethylphenylsilyl)methyl>hexahydrocyclopentapyrrole 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: 65.0%

: (S)-2-<6-(dimethylphenylsilyl)-hex-4-en>-N-<(4-methylphenyl)sulfonyl>-aziridine

: 4-Methyl-N-((1S,2S)-2-vinyl-cyclopentylmethyl)-benzenesulfonamide

: 4-Methyl-N-((1S,2R)-2-vinyl-cyclopentylmethyl)-benzenesulfonamide

: 237404-25-0
(1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-<(dimethylphenylsilyl)methyl>hexahydrocyclopentapyrrole

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 1h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1016/S0040-4020(99)00425-1

Reference yield:

: 1833-51-8
chloromethyldimethylphenylsilane

: 237404-25-0
(1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-<(dimethylphenylsilyl)methyl>hexahydrocyclopentapyrrole

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) Mg, ethylene bromide, 2.) <1,2-bis(Ph₂P)ethane>NiCl₂ / 1.) Et₂O, reflux, 3 h, 2.) benzene, reflux, 30 min, 3.) reflux, 10 h

2: Et₃N, DMAP / CH₂Cl₂ / 4 h / 0 °C

3: NaI / acetone / 2 h / Heating

4: 1.) t-BuLi, 2.) CuI/n-Bu₃P / 1.) pentane, Et₂O, -78 deg C, 10 min, room temperature, 60 min, 2.) Et₂O, -40 deg C, 10 min, -78 deg C, 40 min, 3.) THF, Et₂O, -78 deg C, 60 min

5: 65 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / 0 °C

With dmap; copper(l) iodide; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; tributylphosphine; boron trifluoride diethyl etherate; tert.-butyl lithium; magnesium; ethylene dibromide; triethylamine; sodium iodide; In dichloromethane; acetone;
DOI:10.1016/S0040-4020(99)00425-1

Reference yield:

: 1-iodo-5-(dimethylphenylsilyl)-pent-3-ene

: 237404-25-0
(1S,3aS,6aR)-N-<(4-methylphenyl)sulfonyl>-1-<(dimethylphenylsilyl)methyl>hexahydrocyclopentapyrrole

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) t-BuLi, 2.) CuI/n-Bu₃P / 1.) pentane, Et₂O, -78 deg C, 10 min, room temperature, 60 min, 2.) Et₂O, -40 deg C, 10 min, -78 deg C, 40 min, 3.) THF, Et₂O, -78 deg C, 60 min

2: 65 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / 0 °C

With copper(l) iodide; tributylphosphine; boron trifluoride diethyl etherate; tert.-butyl lithium; In dichloromethane;
DOI:10.1016/S0040-4020(99)00425-1