ethyl 2-((3R,4S)-1-benzoyl-3-((tert-butyldimethylsilyloxy)methyl)piperidin-4-yl)acetate

Base Information

• Chemical Name: ethyl 2-((3R,4S)-1-benzoyl-3-((tert-butyldimethylsilyloxy)methyl)piperidin-4-yl)acetate
• CAS No.: 1269788-51-3
• Molecular Formula: C₂₃H₃₇NO₄Si
• Molecular Weight: 419.637
• Mol file: 1269788-51-3.mol

Synonyms:ethyl 2-((3R,4S)-1-benzoyl-3-((tert-butyldimethylsilyloxy)methyl)piperidin-4-yl)acetate

Chemical Property of ethyl 2-((3R,4S)-1-benzoyl-3-((tert-butyldimethylsilyloxy)methyl)piperidin-4-yl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-((3R,4S)-1-benzoyl-3-((tert-butyldimethylsilyloxy)methyl)piperidin-4-yl)acetate

There total 1 articles about ethyl 2-((3R,4S)-1-benzoyl-3-((tert-butyldimethylsilyloxy)methyl)piperidin-4-yl)acetate 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: 4.97%

C16H33NO3Si + benzoyl chloride (98-88-4) → ethyl 2-((3R,4S)-1-benzoyl-3-((tert-butyldimethylsilyloxy)methyl)piperidin-4-yl)acetate (1269788-51-3)

Guidance literature:

With pyridine; dmap; at 0 - 20 ℃; for 0.75h; optical yield given as %ee; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.12.066

Reference yield: 98.0%

ethyl 2-((3R,4S)-1-benzoyl-3-((tert-butyldimethylsilyloxy)methyl)piperidin-4-yl)acetate (1269788-51-3) + 6-methoxy-4-methylquinoline (41037-26-7) → C32H42N2O4Si (1269788-52-4)

Guidance literature:

6-methoxy-4-methylquinoline; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

ethyl 2-((3R,4S)-1-benzoyl-3-((tert-butyldimethylsilyloxy)methyl)piperidin-4-yl)acetate; In tetrahydrofuran; hexane; at -65 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.12.066

Reference yield:

ethyl 2-((3R,4S)-1-benzoyl-3-((tert-butyldimethylsilyloxy)methyl)piperidin-4-yl)acetate (1269788-51-3) → 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 13 steps

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

1.2: 12 h / -65 °C / Inert atmosphere

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

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

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

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

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

6.2: 3 h / 20 °C / Inert atmosphere

6.3: 2 h / 20 °C / Inert atmosphere

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

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

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

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

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

11.2: -78 - 0 °C / Inert atmosphere

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

12.2: 0.5 h / 0 °C

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

With pyridine; hydrogenchloride; methanol; Trimethyl orthoacetate; dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; methanesulfonamide; potassium tert-butylate; 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; toluene; tert-butyl alcohol; 11.1: Swern oxidation / 11.2: Swern oxidation / 12.1: Wittig reaction / 12.2: Wittig reaction;

DOI:10.1016/j.tetlet.2010.12.066

upstream raw materials:

benzoyl chloride

Downstream raw materials:

quinindine

quinidine acetate

C₃₂H₄₂N₂O₄Si

Refernces