3-(tert-butyldiphenylsilanyloxymethyl)-2-azabicyclo[3.1.0]-hexane-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 3-(tert-butyldiphenylsilanyloxymethyl)-2-azabicyclo[3.1.0]-hexane-2-carboxylic acid tert-butyl ester
• CAS No.: 197142-32-8
• Molecular Formula: C₂₇H₃₇NO₃Si
• Molecular Weight: 451.681
• Mol file: 197142-32-8.mol

Synonyms:3-(tert-butyldiphenylsilanyloxymethyl)-2-azabicyclo[3.1.0]-hexane-2-carboxylic acid tert-butyl ester

Chemical Property of 3-(tert-butyldiphenylsilanyloxymethyl)-2-azabicyclo[3.1.0]-hexane-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(tert-butyldiphenylsilanyloxymethyl)-2-azabicyclo[3.1.0]-hexane-2-carboxylic acid tert-butyl ester

There total 14 articles about 3-(tert-butyldiphenylsilanyloxymethyl)-2-azabicyclo[3.1.0]-hexane-2-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: 90.7%

Chloroiodomethane (593-71-5) + tert-butyl (2S)-2-[[(tert-butyldiphenylsilyl)oxy]methyl]-2,3-dihydro-1H-pyrrole-1-carboxylate → 3-(tert-butyldiphenylsilanyloxymethyl)-2-azabicyclo[3.1.0]-hexane-2-carboxylic acid tert-butyl ester (197142-32-8)

Guidance literature:

With diethylzinc; In toluene; at -25 - -21 ℃; for 19.5h;

Reference yield: 59.0%

diiodomethane (75-11-6) + tert-butyl (2S)-2-[[(tert-butyldiphenylsilyl)oxy]methyl]-2,3-dihydro-1H-pyrrole-1-carboxylate → 3-(tert-butyldiphenylsilanyloxymethyl)-2-azabicyclo[3.1.0]-hexane-2-carboxylic acid tert-butyl ester (197142-32-8)

Guidance literature:

With diethylzinc; In dichloromethane; at 0 - 20 ℃; for 4.5h;

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → 3-(tert-butyldiphenylsilanyloxymethyl)-2-azabicyclo[3.1.0]-hexane-2-carboxylic acid tert-butyl ester (197142-32-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap; triethylamine / dichloromethane / 20 °C

2.1: dmap; triethylamine / dichloromethane / 18 h / 24 °C

3.1: lithium triethylborohydride / toluene; tetrahydrofuran / 1.08 h / -55 - -45 °C

3.2: 14 h / -50 - 20 °C

4.1: diethylzinc / toluene / 19.5 h / -25 - -21 °C

With dmap; diethylzinc; lithium triethylborohydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

upstream raw materials:

trimethylstannylmethyl iodide

(S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate

Chloroiodomethane

tert-butylchlorodiphenylsilane

Downstream raw materials:

3-(6-chloropyridine-3-yloxymethyl)-2-azabicyclo[3.1.0]-hexane hydrochloride

C₂₇H₃₇BN₄O₅

C₂₁H₂₄ClIN₄O₃

C₂₁H₂₅IN₄O₃