(1R,2S,3R,4S)-1,7,7-Trimethyl-3-[N-((S)-1-phenyl-but-3-enyl)aminosulfanyl]-bicyclo[2.2.1]heptan-2-ol

Base Information

• Chemical Name: (1R,2S,3R,4S)-1,7,7-Trimethyl-3-[N-((S)-1-phenyl-but-3-enyl)aminosulfanyl]-bicyclo[2.2.1]heptan-2-ol
• CAS No.: 155234-18-7
• Molecular Formula: C₂₀H₂₉NOS
• Molecular Weight: 331.522
• Mol file: 155234-18-7.mol

Synonyms:(1R,2S,3R,4S)-1,7,7-Trimethyl-3-[N-((S)-1-phenyl-but-3-enyl)aminosulfanyl]-bicyclo[2.2.1]heptan-2-ol

Chemical Property of (1R,2S,3R,4S)-1,7,7-Trimethyl-3-[N-((S)-1-phenyl-but-3-enyl)aminosulfanyl]-bicyclo[2.2.1]heptan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3R,4S)-1,7,7-Trimethyl-3-[N-((S)-1-phenyl-but-3-enyl)aminosulfanyl]-bicyclo[2.2.1]heptan-2-ol

There total 2 articles about (1R,2S,3R,4S)-1,7,7-Trimethyl-3-[N-((S)-1-phenyl-but-3-enyl)aminosulfanyl]-bicyclo[2.2.1]heptan-2-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: 75.0%

C17H23NOS (155234-13-2) + allylmagnesium bromide (1730-25-2) → (1R,2S,3R,4S)-1,7,7-Trimethyl-3-[N-((S)-1-phenyl-but-3-enyl)aminosulfanyl]-bicyclo[2.2.1]heptan-2-ol (155234-18-7)

Guidance literature:

In tetrahydrofuran; for 0.5h;

DOI:10.1021/jo00083a037

Reference yield:

(1R,2S,3R)-3-mercapto-1,7,7-trimethylbicyclo{2.2.1}heptan-2-ol (132609-85-9) → (1R,2S,3R,4S)-1,7,7-Trimethyl-3-[N-((S)-1-phenyl-but-3-enyl)aminosulfanyl]-bicyclo[2.2.1]heptan-2-ol (155234-18-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 58 percent / N-chlorosuccinimide, NH₃ / tetrahydrofuran / 0.5 h / -33 °C

2: CH₂Cl₂; tetrahydrofuran / 28 h / Ambient temperature

3: 75 percent / tetrahydrofuran / 0.5 h

With N-chloro-succinimide; ammonia; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00083a037

Reference yield: 99.0%

(1R,2S,3R,4S)-1,7,7-Trimethyl-3-[N-((S)-1-phenyl-but-3-enyl)aminosulfanyl]-bicyclo[2.2.1]heptan-2-ol (155234-18-7) → (S)-1-phenylbut-3-en-1-amine (4383-23-7,110216-57-4,115224-13-0,130608-03-6) + (1R,2S,3R)-bis(2-hydroxybornane-3-yl)disulfide (502917-77-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 3h;

DOI:10.1021/jo00083a037

upstream raw materials:

C₁₇H₂₃NOS

allylmagnesium bromide

(1R,2S,3R)-3-mercapto-1,7,7-trimethylbicyclo{2.2.1}heptan-2-ol

Downstream raw materials:

(S)-1-phenylbut-3-en-1-amine

(1R,2S,3R)-bis(2-hydroxybornane-3-yl)disulfide

(1R,2S,3R)-3-Mercapto-2-(benzyloxy)-1,7,7-trimethylbicyclo<2.2.1>heptane

S-((1S,2R,3S,4R)-3-Benzyloxy-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-thiohydroxylamine