1-[3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,6,6-trimethyl-cyclohexa-1,4-dienyl]-1-pyrrolidin-1-yl-methanone

Base Information

• Chemical Name: 1-[3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,6,6-trimethyl-cyclohexa-1,4-dienyl]-1-pyrrolidin-1-yl-methanone
• CAS No.: 310889-34-0
• Molecular Formula: C₃₈H₄₇NO₃Si
• Molecular Weight: 593.882
• Mol file: 310889-34-0.mol

Synonyms:1-[3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,6,6-trimethyl-cyclohexa-1,4-dienyl]-1-pyrrolidin-1-yl-methanone

Chemical Property of 1-[3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,6,6-trimethyl-cyclohexa-1,4-dienyl]-1-pyrrolidin-1-yl-methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,6,6-trimethyl-cyclohexa-1,4-dienyl]-1-pyrrolidin-1-yl-methanone

There total 10 articles about 1-[3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,6,6-trimethyl-cyclohexa-1,4-dienyl]-1-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: 100.0%

pyrrolidine (123-75-1) + (3aS,7S,7aR)-7-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-3a-chloro-4,4,7a-trimethyl-3a,4,7,7a-tetrahydro-isobenzofuran-1,3-dione → 1-[3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,6,6-trimethyl-cyclohexa-1,4-dienyl]-1-pyrrolidin-1-yl-methanone (310889-34-0)

Guidance literature:

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; dimethyl sulfoxide; at 20 ℃; for 2h;

DOI:10.1039/b005533f

Reference yield:

2-(Isopropylidene)-1,3-propanediol (2035-85-0) → 1-[3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,6,6-trimethyl-cyclohexa-1,4-dienyl]-1-pyrrolidin-1-yl-methanone (310889-34-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: tetrahydrofuran / 15 h / 20 °C

2.1: TPAP; NMO; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 20 °C

3.1: LDA / tetrahydrofuran / -78 °C

3.2: Benzoyl chloride / tetrahydrofuran / 0.92 h / -78 - 20 °C

3.3: SmI₂; DMPU / tetrahydrofuran / 1 h / 20 °C

4.1: 66 percent / toluene / 24 h / 150 °C

5.1: 86 percent / tetrahydrofuran / 1 h / 20 °C

6.1: i-BuOCOCl; NEt₃ / CH₂Cl₂ / 2 h / 20 °C

7.1: 87 percent / NCS; NEt₃; H₂O / tetrahydrofuran / 1 h / 0 °C

8.1: 100 percent / DMPU; DMSO / 2 h / 20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-chloro-succinimide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; water; sodium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; toluene; 1.1: Metallation / 1.2: Etherification / 2.1: Oxidation / 3.1: Metallation / 3.2: Substitution / 3.3: Oxidation / 4.1: Cycloaddition / 5.1: Ring cleavage / 6.1: Cyclization / 7.1: Chlorination / 8.1: Ring cleavage;

DOI:10.1039/b005533f

Reference yield:

(((benzyloxy)methyl)sulfonyl)benzene (131186-52-2) → 1-[3-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,6,6-trimethyl-cyclohexa-1,4-dienyl]-1-pyrrolidin-1-yl-methanone (310889-34-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: LDA / tetrahydrofuran / -78 °C

1.2: Benzoyl chloride / tetrahydrofuran / 0.92 h / -78 - 20 °C

1.3: SmI₂; DMPU / tetrahydrofuran / 1 h / 20 °C

2.1: 66 percent / toluene / 24 h / 150 °C

3.1: 86 percent / tetrahydrofuran / 1 h / 20 °C

4.1: i-BuOCOCl; NEt₃ / CH₂Cl₂ / 2 h / 20 °C

5.1: 87 percent / NCS; NEt₃; H₂O / tetrahydrofuran / 1 h / 0 °C

6.1: 100 percent / DMPU; DMSO / 2 h / 20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-chloro-succinimide; water; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; toluene; 1.1: Metallation / 1.2: Substitution / 1.3: Oxidation / 2.1: Cycloaddition / 3.1: Ring cleavage / 4.1: Cyclization / 5.1: Chlorination / 6.1: Ring cleavage;

DOI:10.1039/b005533f

upstream raw materials:

pyrrolidine

2-(Isopropylidene)-1,3-propanediol

(((benzyloxy)methyl)sulfonyl)benzene

tert-butylchlorodiphenylsilane