(3R,5S,7S,7aS,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-decahydro-pyrrolo[2,1-j]quinoline

Base Information

• Chemical Name: (3R,5S,7S,7aS,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-decahydro-pyrrolo[2,1-j]quinoline
• CAS No.: 780820-96-4
• Molecular Formula: C₄₁H₆₄BNO₃Si
• Molecular Weight: 657.861
• Mol file: 780820-96-4.mol

Synonyms:(3R,5S,7S,7aS,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-decahydro-pyrrolo[2,1-j]quinoline

Chemical Property of (3R,5S,7S,7aS,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-decahydro-pyrrolo[2,1-j]quinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S,7S,7aS,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-decahydro-pyrrolo[2,1-j]quinoline

There total 15 articles about (3R,5S,7S,7aS,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-decahydro-pyrrolo[2,1-j]quinoline 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%

[(3R,5S,7S,7aS,11aR)-5-Hexyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-decahydro-pyrrolo[2,1-j]quinolin-3-yl]-methanol (780820-95-3) + tert-butylchlorodiphenylsilane (58479-61-1) → (3R,5S,7S,7aS,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-decahydro-pyrrolo[2,1-j]quinoline (780820-96-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1002/anie.200460178

Reference yield:

3-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-4-thia-3a-aza-cyclopenta[c]indene 4,4-dioxide (780820-85-1) → (3R,5S,7S,7aS,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-decahydro-pyrrolo[2,1-j]quinoline (780820-96-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: t-BuLi / pentane; tetrahydrofuran / 0.25 h / -78 °C

1.2: BF₃*Et₂O / pentane; tetrahydrofuran / 3 h / -78 - 0 °C

2.1: 381 mg / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

3.1: DBU / dimethylformamide / 0.17 h

3.2: 86 percent / CuCl; potassium acetate / dimethylformamide / 0.33 h

4.1: 95 percent / TBAF / tetrahydrofuran / 5 h / 25 °C

5.1: 73 percent / NaBH(OAc)3; AcOH / CH₂Cl₂ / 12 h / -78 - 25 °C

6.1: 95 percent / imidazole / dimethylformamide / 3 h / 25 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium tris(acetoxy)borohydride; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; pentane; 3.2: Miyaura borylation;

DOI:10.1016/j.tet.2006.01.111

Reference yield:

1-[(3R,5S,5aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dioxo-octahydro-4λ6-thia-3a-aza-cyclopenta[c]inden-5-yl]-octan-2-ol (780820-87-3) → (3R,5S,7S,7aS,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-decahydro-pyrrolo[2,1-j]quinoline (780820-96-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 381 mg / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

2.1: DBU / dimethylformamide / 0.17 h

2.2: 86 percent / CuCl; potassium acetate / dimethylformamide / 0.33 h

3.1: 95 percent / TBAF / tetrahydrofuran / 5 h / 25 °C

4.1: 73 percent / NaBH(OAc)3; AcOH / CH₂Cl₂ / 12 h / -78 - 25 °C

5.1: 95 percent / imidazole / dimethylformamide / 3 h / 25 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2.2: Miyaura borylation;

DOI:10.1016/j.tet.2006.01.111

upstream raw materials:

[(3R,5S,7S,7aS,11aR)-5-Hexyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-decahydro-pyrrolo[2,1-j]quinolin-3-yl]-methanol

tert-butylchlorodiphenylsilane

3-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-4-thia-3a-aza-cyclopenta[c]indene 4,4-dioxide

(S)-1-((2R,5R,6S)-2-Hydroxymethyl-1-aza-spiro[4.5]dec-6-yl)-1-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nonan-3-one

Downstream raw materials:

(3R,5S,7aR,11aR)-3-[[(tert-butyldiphenylsilyl)oxy]methyl]-5-hexyloctahydro-pyrrolo-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

(3R,5S,7aR,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-decahydro-pyrrolo[2,1-j]quinolin-7-ol