tert-butyl methyl((S)-1-oxo-1-((3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylamino)hexan-2-yl)carbamate

Base Information

• Chemical Name: tert-butyl methyl((S)-1-oxo-1-((3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylamino)hexan-2-yl)carbamate
• CAS No.: 1228027-28-8
• Molecular Formula: C₂₆H₃₈F₃N₃O₅S
• Molecular Weight: 561.666
• Mol file: 1228027-28-8.mol

Synonyms:

Chemical Property of tert-butyl methyl((S)-1-oxo-1-((3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylamino)hexan-2-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl methyl((S)-1-oxo-1-((3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylamino)hexan-2-yl)carbamate

There total 10 articles about tert-butyl methyl((S)-1-oxo-1-((3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylamino)hexan-2-yl)carbamate 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:

(3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine (1228030-25-8) + N-BOC-N-methylnorleucine (117903-25-0) → tert-butyl methyl((S)-1-oxo-1-((3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylamino)hexan-2-yl)carbamate (1228027-28-8)

Guidance literature:

With benzotriazol-1-ol; 1,2-dichloro-ethane; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/j.bmcl.2013.06.074

Reference yield:

(3aR,6aS)-2-benzyl-tetrahydrocyclopenta[c]pyrrol-4(1H,2H,5H)-one → tert-butyl methyl((S)-1-oxo-1-((3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylamino)hexan-2-yl)carbamate (1228027-28-8)

Guidance literature:

Multi-step reaction with 9 steps

1: sodium tetrahydroborate / methanol / 16 h / -78 - 20 °C

2: triethylamine / dichloromethane / 0.5 h / 25 °C

3: sodium azide / N,N-dimethyl acetamide / 16 h / 90 °C

4: triphenylphosphine; water / tetrahydrofuran / 1 h / 80 °C

5: triethylamine / dichloromethane

6: 20% palladium hydroxide-activated charcoal; hydrogen / ethanol / 4 h / 20 °C / 1551.49 Torr

7: triethylamine / 3 h / 20 °C

8: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C

9: 1,2-dichloro-ethane; benzotriazol-1-ol / dichloromethane / 16 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; sodium azide; 20% palladium hydroxide-activated charcoal; water; hydrogen; benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl acetamide; 4: |Staudinger Azide Reduction;

DOI:10.1016/j.bmcl.2013.06.074

Reference yield:

(3aR,4R,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ol (1349980-80-8) → tert-butyl methyl((S)-1-oxo-1-((3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylamino)hexan-2-yl)carbamate (1228027-28-8)

Guidance literature:

Multi-step reaction with 8 steps

1: triethylamine / dichloromethane / 0.5 h / 25 °C

2: sodium azide / N,N-dimethyl acetamide / 16 h / 90 °C

3: triphenylphosphine; water / tetrahydrofuran / 1 h / 80 °C

4: triethylamine / dichloromethane

5: 20% palladium hydroxide-activated charcoal; hydrogen / ethanol / 4 h / 20 °C / 1551.49 Torr

6: triethylamine / 3 h / 20 °C

7: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C

8: 1,2-dichloro-ethane; benzotriazol-1-ol / dichloromethane / 16 h / 20 °C

With hydrogenchloride; sodium azide; 20% palladium hydroxide-activated charcoal; water; hydrogen; benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl acetamide; 3: |Staudinger Azide Reduction;

DOI:10.1016/j.bmcl.2013.06.074

upstream raw materials:

(3aR,4R,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ol

C₁₅H₂₁NO₃S

(3aR,4S,6aS)-2-(phenylmethyl)octahydrocyclopenta[c]pyrrol-4-amine

tert-butyl (3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylcarbamate

Downstream raw materials:

N₂-methyl-N₁-((3aR,4S,6aS)-2-{[4-(trifluoromethyl)phenyl]sulfonyl}octahydrocyclopenta[c]pyrrol-4-yl)-L-norleucinamide

Refernces

• 1、 -. "NOVEL SUBSTITUTED OCTAHYDROCYCLOPENTA[C]PYRROL-4-AMINES AS CALCIUM CHANNEL BLOCKERS". Page/Page column 104. . Retrieved 2010/06/14.