benzyl (R,Z)-3-((tert-butyldimethylsilyloxy)methyl)-4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate

Base Information

• Chemical Name: benzyl (R,Z)-3-((tert-butyldimethylsilyloxy)methyl)-4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate
• CAS No.: 1269788-48-8
• Molecular Formula: C₂₄H₃₇NO₅Si
• Molecular Weight: 447.647
• Mol file: 1269788-48-8.mol

Synonyms:benzyl (R,Z)-3-((tert-butyldimethylsilyloxy)methyl)-4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate

Chemical Property of benzyl (R,Z)-3-((tert-butyldimethylsilyloxy)methyl)-4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (R,Z)-3-((tert-butyldimethylsilyloxy)methyl)-4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate

There total 1 articles about benzyl (R,Z)-3-((tert-butyldimethylsilyloxy)methyl)-4-(2-ethoxy-2-oxoethylidene)piperidine-1-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: 100.0%

trimethylsilanyl-acetic acid ethyl ester (4071-88-9) + benzyl (R)-3-(tert-butyldimethylsilyloxymethyl)-4-oxopiperidine-1-carboxylate (1269788-45-5) → benzyl (R,Z)-3-((tert-butyldimethylsilyloxy)methyl)-4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate (1269788-48-8)

Guidance literature:

trimethylsilanyl-acetic acid ethyl ester; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

benzyl (R)-3-(tert-butyldimethylsilyloxymethyl)-4-oxopiperidine-1-carboxylate; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.12.066

Reference yield:

benzyl (R,Z)-3-((tert-butyldimethylsilyloxy)methyl)-4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate (1269788-48-8) → quinindine (56-54-2,130-95-0,572-59-8,572-60-1,42151-59-7,47342-58-5,72402-50-7,72402-51-8,72402-52-9,72402-53-0,101143-86-6,101143-87-7,101143-88-8,146925-10-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 6 h / 20 °C / Inert atmosphere

2.1: pyridine; dmap / 0.75 h / 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

3.2: 12 h / -65 °C / Inert atmosphere

4.1: sodium tetrahydroborate / methanol / 2 h / 20 °C / Cooling with ice; Inert atmosphere

5.1: pyridine / 1.5 h / 0 - 20 °C / Inert atmosphere

6.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

7.1: methanesulfonamide; hydroquinidein 1,4-phthalazinediyl diether / water; tert-butyl alcohol / 72 h / 4 °C / Inert atmosphere

8.1: Trimethyl orthoacetate; pyridinium p-toluenesulfonate / dichloromethane / 5 h / 20 °C / Inert atmosphere

8.2: 3 h / 20 °C / Inert atmosphere

8.3: 2 h / 20 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / hexane; toluene / 0.33 h / -78 °C / Inert atmosphere

10.1: N,N-dimethyl-formamide / 4 h / Reflux; Inert atmosphere

11.1: dmap; triethylamine / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

12.1: hydrogenchloride; methanol / 5 h / 20 °C / Inert atmosphere

13.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere

13.2: -78 - 0 °C / Inert atmosphere

14.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

14.2: 0.5 h / 0 °C

15.1: methanol; potassium carbonate / 1.5 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; methanol; Trimethyl orthoacetate; dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; methanesulfonamide; 20 % Pd(OH)2/C; potassium tert-butylate; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; 13.1: Swern oxidation / 13.2: Swern oxidation / 14.1: Wittig reaction / 14.2: Wittig reaction;

DOI:10.1016/j.tetlet.2010.12.066

Reference yield:

benzyl (R,Z)-3-((tert-butyldimethylsilyloxy)methyl)-4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate (1269788-48-8) → C32H44N2O5Si (1269788-54-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 6 h / 20 °C / Inert atmosphere

2.1: pyridine; dmap / 0.75 h / 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

3.2: 12 h / -65 °C / Inert atmosphere

4.1: sodium tetrahydroborate / methanol / 2 h / 20 °C / Cooling with ice; Inert atmosphere

5.1: pyridine / 1.5 h / 0 - 20 °C / Inert atmosphere

6.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

7.1: methanesulfonamide; 1,4-bis(9-O-dihydroquinidine)phthalazine / water; tert-butyl alcohol / 48 h / 4 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; n-butyllithium; methanesulfonamide; 20 % Pd(OH)2/C; potassium tert-butylate; hydrogen; 1,4-bis(9-O-dihydroquinidine)phthalazine; diisopropylamine; In tetrahydrofuran; methanol; hexane; water; ethyl acetate; tert-butyl alcohol;

DOI:10.1016/j.tetlet.2010.12.066

upstream raw materials:

trimethylsilanyl-acetic acid ethyl ester

benzyl (R)-3-(tert-butyldimethylsilyloxymethyl)-4-oxopiperidine-1-carboxylate

Downstream raw materials:

C₃₂H₄₄N₂O₅Si

quinindine

quinidine acetate

Refernces