4-[hydroxy-(4-trifluoromethyl-phenyl)-methyl]-4'-methyl-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

Base Information

Chemical Name:4-[hydroxy-(4-trifluoromethyl-phenyl)-methyl]-4'-methyl-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester
CAS No.:438208-26-5
Molecular Formula:C₂₄H₃₅F₃N₂O₃
Molecular Weight:456.549
Hs Code.:

4-[hydroxy-(4-trifluoromethyl-phenyl)-methyl]-4'-methyl-[1,4']bipiperidinyl-1'-carboxylic acid <i>tert</i>-butyl ester

Synonyms:4-[hydroxy-(4-trifluoromethyl-phenyl)-methyl]-4'-methyl-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

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Chemical Property of 4-[hydroxy-(4-trifluoromethyl-phenyl)-methyl]-4'-methyl-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

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Technology Process of 4-[hydroxy-(4-trifluoromethyl-phenyl)-methyl]-4'-methyl-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

There total 4 articles about 4-[hydroxy-(4-trifluoromethyl-phenyl)-methyl]-4'-methyl-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl 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: 62.0%

: 402-43-7
p-trifluoromethylphenyl bromide

: 305794-51-8
4-formyl-1'-(tert-butoxycarbonyl)-4'-methyl-1,4'-bipiperidine

: 438208-26-5
4-[hydroxy-(4-trifluoromethyl-phenyl)-methyl]-4'-methyl-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

Guidance literature:: p-trifluoromethylphenyl bromide; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.333333h;

4-formyl-1'-(tert-butoxycarbonyl)-4'-methyl-1,4'-bipiperidine; In tetrahydrofuran; at -78 - 20 ℃; for 2h; Further stages.;
DOI:10.1021/jm0200815

Reference yield:

: 148133-82-8
4-methylene piperidine

: 438208-26-5
4-[hydroxy-(4-trifluoromethyl-phenyl)-methyl]-4'-methyl-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: DBU; Ti(OiPr)4 / 1,2-dichloro-ethane / 18 h / 20 °C

2.1: 20.0 g / 3 h / 20 °C

3.1: 90 percent / MeMgBr / tetrahydrofuran; diethyl ether / 2 h / 20 °C

4.1: BH₃*THF / tetrahydrofuran / 18 h / 0 - 20 °C

4.2: 41 percent / 30percent aq. H₂O₂ / tetrahydrofuran; ethanol / 24 h / 20 °C / pH 7

5.1: NMO; tetrapropylammonium perruthenate / CH₂Cl₂ / 1 h / 20 °C

6.1: n-BuLi / tetrahydrofuran / 0.33 h / -78 °C

6.2: 62 percent / tetrahydrofuran / 2 h / -78 - 20 °C

With titanium(IV) isopropylate; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane-THF; methylmagnesium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/jm0200815

Reference yield:

: 305794-50-7
4-hydroxymethyl-4'-methyl-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

: 438208-26-5
4-[hydroxy-(4-trifluoromethyl-phenyl)-methyl]-4'-methyl-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: NMO; tetrapropylammonium perruthenate / CH₂Cl₂ / 1 h / 20 °C

2.1: n-BuLi / tetrahydrofuran / 0.33 h / -78 °C

2.2: 62 percent / tetrahydrofuran / 2 h / -78 - 20 °C

With n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jm0200815