{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-phenyl}-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

Base Information

• Chemical Name: {2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-phenyl}-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone
• CAS No.: 145105-09-5
• Molecular Formula: C₂₂H₃₇NO₃Si
• Molecular Weight: 391.626
• Mol file: 145105-09-5.mol

Synonyms:{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-phenyl}-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

Chemical Property of {2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-phenyl}-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-phenyl}-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

There total 1 articles about {2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-phenyl}-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone 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:

7-methyl-3,4-dihydro-1H-2-benzopyran-1-one (66122-71-2) + (2S)-2-(methoxymethyl)-1-pyrrolidine (63126-47-6) + tert-butyldimethylsilyl chloride (18162-48-6) → {2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-phenyl}-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone (145105-09-5)

Guidance literature:

Multistep reaction; 1.) lithium amide formation;

DOI:10.1016/S0040-4039(00)60998-X

Reference yield:

{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-phenyl}-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone (145105-09-5) → (2S,4S,5S)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-2,4-dimethyl-cyclohexanone (145105-15-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) K, NH₃ / 1.) THF, t-BuOH

2: 98 percent / PDC, t-BuOOH, Celite / benzene

3: 100 percent / H₂ / 3)>PF₆ / CH₂Cl₂ / 760 Torr

With tert.-butylhydroperoxide; dipyridinium dichromate; Celite; ammonia; hydrogen; (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate; In dichloromethane; benzene;

DOI:10.1016/S0040-4039(00)60998-X

Reference yield:

{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-phenyl}-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone (145105-09-5) → (2S,4S,5R)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-2,4-dimethyl-cyclohexanone (145105-24-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) K, NH₃ / 1.) THF, t-BuOH

2: 98 percent / PDC, t-BuOOH, Celite / benzene

3: 3 percent / H₂ / Rh/Al₂O₃ / ethyl acetate / 2844.3 Torr

With tert.-butylhydroperoxide; dipyridinium dichromate; Celite; ammonia; hydrogen; Rh/Al₂O₃; In ethyl acetate; benzene;

DOI:10.1016/S0040-4039(00)60998-X

upstream raw materials:

7-methyl-3,4-dihydro-1H-2-benzopyran-1-one

(2S)-2-(methoxymethyl)-1-pyrrolidine

tert-butyldimethylsilyl chloride

Downstream raw materials:

{(S)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1,5-dimethyl-cyclohexa-2,5-dienyl}-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

(S)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-2,4-dimethyl-cyclohexa-2,5-dienone

(2S,4S,5R)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-2,4-dimethyl-cyclohexanone

(2R,4S,5R)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-2,4-dimethyl-cyclohexanone