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

Base Information

• Chemical Name: (3R,5S,7aR,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-decahydro-pyrrolo[2,1-j]quinolin-7-ol
• CAS No.: 780820-99-7
• Molecular Formula: C₃₅H₅₃NO₂Si
• Molecular Weight: 547.897
• Mol file: 780820-99-7.mol

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

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

There total 14 articles about (3R,5S,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: 97.0%

(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) → (3R,5S,7aR,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-decahydro-pyrrolo[2,1-j]quinolin-7-ol (780820-99-7)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1002/anie.200460178

Reference yield:

(R)-2-Hydroxymethyl-1-methanesulfonyl-1-aza-spiro[4.5]deca-6,9-dien-8-one (780820-77-1) → (3R,5S,7aR,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-decahydro-pyrrolo[2,1-j]quinolin-7-ol (780820-99-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 1.56 g / imidazole / dimethylformamide / 3 h / 20 °C

2.1: potassium hexamethyldisilazide / tetrahydrofuran / 8 h / -100 - 0 °C

2.2: BF₃*Et₂O; thiophenol / CH₂Cl₂ / 0 - 20 °C

2.3: 623 mg / Raney nickel / ethyl acetate; ethanol / 4 h / 20 °C

3.1: t-BuLi / tetrahydrofuran / 0.25 h / -78 °C

3.2: BF₃*Et₂O / tetrahydrofuran / 3 h / -78 - 0 °C

4.1: 381 g / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide

5.2: 86 percent / CuCl; KOAc / dimethylformamide / 0.33 h / 20 °C

6.1: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

7.1: 73 percent / NaBH(OAc)3; AcOH / CH₂Cl₂ / -78 - 20 °C

8.1: 95 percent / imidazole / dimethylformamide / 3 h / 20 °C

9.1: 97 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0.5 h / 0 °C

With 1H-imidazole; sodium hydroxide; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; potassium hexamethylsilazane; 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;

DOI:10.1002/anie.200460178

Reference yield:

(D)-(-)-methyl homotyrosinate (477289-51-3) → (3R,5S,7aR,11aR)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hexyl-decahydro-pyrrolo[2,1-j]quinolin-7-ol (780820-99-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 1.66 g / NEt₃ / CH₂Cl₂ / 4 h / 20 °C

2.1: 94 percent / NaBH₄ / ethanol; tetrahydrofuran / 0 - 20 °C

3.1: 90 percent / aq. NaOH / dioxane / 80 °C

4.1: PhI(OAc)2 / various solvent(s) / 0.5 h / 20 °C

5.1: 1.56 g / imidazole / dimethylformamide / 3 h / 20 °C

6.1: potassium hexamethyldisilazide / tetrahydrofuran / 8 h / -100 - 0 °C

6.2: BF₃*Et₂O; thiophenol / CH₂Cl₂ / 0 - 20 °C

6.3: 623 mg / Raney nickel / ethyl acetate; ethanol / 4 h / 20 °C

7.1: t-BuLi / tetrahydrofuran / 0.25 h / -78 °C

7.2: BF₃*Et₂O / tetrahydrofuran / 3 h / -78 - 0 °C

8.1: 381 g / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide

9.2: 86 percent / CuCl; KOAc / dimethylformamide / 0.33 h / 20 °C

10.1: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

11.1: 73 percent / NaBH(OAc)3; AcOH / CH₂Cl₂ / -78 - 20 °C

12.1: 95 percent / imidazole / dimethylformamide / 3 h / 20 °C

13.1: 97 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0.5 h / 0 °C

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; potassium hexamethylsilazane; sodium tris(acetoxy)borohydride; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200460178

upstream raw materials:

(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

(D)-(-)-methyl homotyrosinate

(R)-2-Hydroxymethyl-1-methanesulfonyl-1-aza-spiro[4.5]deca-6,9-dien-8-one

(D)-(-)-N-methanesulfonyl-homotyrosinol

Downstream raw materials:

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