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

Base Information

• Chemical Name: (3R,5R,7S,7aR,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-decahydro-pyrrolo[2,1-j]quinolin-7-ol
• CAS No.: 780820-92-0
• Molecular Formula: C₃₅H₅₃NO₂Si
• Molecular Weight: 547.897
• Mol file: 780820-92-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

3-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-4-thia-3a-aza-cyclopenta[c]indene 4,4-dioxide (780820-85-1) → (3R,5R,7S,7aR,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-decahydro-pyrrolo[2,1-j]quinolin-7-ol (780820-92-0)

Guidance literature:

Multi-step reaction with 4 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: sodium cyanoborohydride; AcOH / methanol / 4 h / 0 °C

4.2: 80 percent / NaOH; H₂O₂ / methanol; H₂O / 0.5 h / 0 °C

With tert.-butyl lithium; sodium cyanoborohydride; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; 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-one (780820-89-5) → (3R,5R,7S,7aR,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-decahydro-pyrrolo[2,1-j]quinolin-7-ol (780820-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DBU / dimethylformamide / 0.17 h

1.2: 86 percent / CuCl; potassium acetate / dimethylformamide / 0.33 h

2.1: sodium cyanoborohydride; AcOH / methanol / 4 h / 0 °C

2.2: 80 percent / NaOH; H₂O₂ / methanol; H₂O / 0.5 h / 0 °C

With sodium cyanoborohydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; N,N-dimethyl-formamide; 1.2: 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,5R,7S,7aR,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-decahydro-pyrrolo[2,1-j]quinolin-7-ol (780820-92-0)

Guidance literature:

Multi-step reaction with 3 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: sodium cyanoborohydride; AcOH / methanol / 4 h / 0 °C

3.2: 80 percent / NaOH; H₂O₂ / methanol; H₂O / 0.5 h / 0 °C

With sodium cyanoborohydride; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; N,N-dimethyl-formamide; 2.2: Miyaura borylation;

DOI:10.1016/j.tet.2006.01.111

upstream raw materials:

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

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-one

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

1,2-Epoxyoctane

Downstream raw materials:

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