1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-5-methoxy-, 1,1-dimethylethyl ester, (2S)-

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-5-methoxy-, 1,1-dimethylethyl ester, (2S)-
• CAS No.: 192389-29-0
• Molecular Formula: C27H39NO4Si
• Molecular Weight: 469.696
• Mol file: 192389-29-0.mol

Synonyms:

Chemical Property of 1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-5-methoxy-, 1,1-dimethylethyl ester, (2S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-5-methoxy-, 1,1-dimethylethyl ester, (2S)-

There total 10 articles about 1-Pyrrolidinecarboxylic acid, 2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-5-methoxy-, 1,1-dimethylethyl ester, (2S)- 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: 95.0%

2,2-dimethoxy-propane (77-76-9) + (5S)-1-(benzyloxycarbonyl)-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-hydroxypyrrolidine (192389-43-8) → (2S,5S/R)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)methyl-5-methoxy-pyrrolidine (192389-29-0)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; for 0.166667h;

DOI:10.1016/S0040-4039(97)00845-9

Reference yield: 90.0%

(5S)-1-(benzyloxycarbonyl)-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-hydroxypyrrolidine (192389-43-8) + trimethyl orthoformate (149-73-5) → (2S,5S/R)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)methyl-5-methoxy-pyrrolidine (192389-29-0)

Guidance literature:

With 3 A molecular sieve; boron trifluoride diethyl etherate; In diethyl ether; at 20 ℃; for 4.5h;

DOI:10.1021/jo062406l

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → (2S,5S/R)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)methyl-5-methoxy-pyrrolidine (192389-29-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / imidazole / dimethylformamide / 18 h / 20 °C

2: 96 percent / DMAP / acetonitrile / 4 h / 20 °C

3: 98 percent / LiEt₃BH / tetrahydrofuran / 0.25 h / -80 °C

4: 90 percent / 3 Angstroem molecular sieves; BF₃*OEt₂ / diethyl ether / 4.5 h / 20 °C

With 1H-imidazole; dmap; 3 A molecular sieve; boron trifluoride diethyl etherate; lithium triethylborohydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo062406l

upstream raw materials:

2,2-dimethoxy-propane

(5S)-1-(benzyloxycarbonyl)-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-hydroxypyrrolidine

trimethyl orthoformate

di-tert-butyl dicarbonate

Downstream raw materials:

(2S,5R)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate

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

(2S,5S,1'S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-(1'-hydroxy-3'-trimethylsilyl)-prop-2'-ynyl-pyrrolidine

(2S,5S,1'R)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)methyl-2-(1'-hydroxy-3'-trimethylsilyl)-prop-2'-ynyl-pyrrolidine