4-[2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl]-piperidine-1,4-dicarboxylic acid 1-benzyl ester 4-ethyl ester

Base Information

• Chemical Name: 4-[2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl]-piperidine-1,4-dicarboxylic acid 1-benzyl ester 4-ethyl ester
• CAS No.: 757239-38-6
• Molecular Formula: C₂₄H₃₉NO₆Si
• Molecular Weight: 465.662
• Mol file: 757239-38-6.mol

Synonyms:4-[2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl]-piperidine-1,4-dicarboxylic acid 1-benzyl ester 4-ethyl ester

Chemical Property of 4-[2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl]-piperidine-1,4-dicarboxylic acid 1-benzyl ester 4-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl]-piperidine-1,4-dicarboxylic acid 1-benzyl ester 4-ethyl ester

There total 1 articles about 4-[2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl]-piperidine-1,4-dicarboxylic acid 1-benzyl ester 4-ethyl 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: 78.0%

tert-butyldimethylsiloxyacetaldehyde (102191-92-4) + 1-benzyl 4-ethyl piperidine-1,4-dicarboxylate (160809-38-1) → 4-[2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl]-piperidine-1,4-dicarboxylic acid 1-benzyl ester 4-ethyl ester (757239-38-6)

Guidance literature:

1-benzyl 4-ethyl piperidine-1,4-dicarboxylate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃; for 1.5h;

tert-butyldimethylsiloxyacetaldehyde; In tetrahydrofuran; at -78 - 20 ℃; for 2.5h;

Reference yield: 73.0%

4-[2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl]-piperidine-1,4-dicarboxylic acid 1-benzyl ester 4-ethyl ester (757239-38-6) → 4-(1,2-dihydroxyethyl)-1-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester (757239-39-7)

Guidance literature:

4-[2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl]-piperidine-1,4-dicarboxylic acid 1-benzyl ester 4-ethyl ester; With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 2h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

Reference yield:

4-[2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl]-piperidine-1,4-dicarboxylic acid 1-benzyl ester 4-ethyl ester (757239-38-6) → 8-[5-[1-(3,5-bis-trifluoromethyl-phenyl)-ethoxy]-4-(4-fluoro-phenyl)-tetrahydro-pyran-3-ylmethyl]-2-oxa-8-aza-spiro[4.5]decan-4-ol

Guidance literature:

Multi-step reaction with 7 steps

1: LiBH₄ / tetrahydrofuran

2: TBAF / tetrahydrofuran

3: 76 percent / DEAD; Ph₃P / tetrahydrofuran

4: 38 percent / Et₃N; DMAP / CH₂Cl₂

5: 100 percent / H₂; TFA / Pd/C / ethanol

6: sodium triacetoxyborohydride / 1,2-dichloro-ethane / 1 h

7: 66 mg / aq. NaOH / methanol / 0.25 h

With dmap; sodium hydroxide; lithium borohydride; tetrabutyl ammonium fluoride; hydrogen; sodium tris(acetoxy)borohydride; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; 3: Mitsunobu reaction;

DOI:10.1055/s-2006-932489

upstream raw materials:

tert-butyldimethylsiloxyacetaldehyde

1-benzyl 4-ethyl piperidine-1,4-dicarboxylate

Downstream raw materials:

4-hydroxy-2-oxa-8-aza-spiro[4.5]decane-8-carboxylic acid benzyl ester

4-(1,2-dihydroxyethyl)-1-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester