CIS-4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-N-BOC-1-NAPHTHALENAMINE

Base Information

• Chemical Name: CIS-4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-N-BOC-1-NAPHTHALENAMINE
• CAS No.: 267884-84-4
• Molecular Formula: C21H23Cl2NO2
• Molecular Weight: 392.325
• Mol file: 267884-84-4.mol

Synonyms:CIS-4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-N-BOC-1-NAPHTHALENAMINE;[(1S,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenyl]carbaMic Acid 1,1-DiMethylethyl Ester

Chemical Property of CIS-4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-N-BOC-1-NAPHTHALENAMINE

Chemical Property:

• Melting Point: 138-140°C
• PSA: 38.33000
• LogP: 6.87580
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

99% ^*data from raw suppliers

cis-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydroN-Boc-1-naphthalenamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate in the synthesis of the drug metabolite Sertraline.

Technology Process of CIS-4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-N-BOC-1-NAPHTHALENAMINE

There total 14 articles about CIS-4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDRO-N-BOC-1-NAPHTHALENAMINE 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:

D-dibenzylaminophenylglycinal (174023-92-8) → cis-(1S,4S)-N-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine (267884-84-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 2.62 g / benzene; CH₂Cl₂ / 15 h / 20 °C

2: 83 percent / Mg / 4 h

3: 76 percent / LiAlH₄ / tetrahydrofuran / 0 - 20 °C

4: 0.85 g / pyridinium dichromate / CH₂Cl₂ / 5 h / 20 °C

5: 1.0 g / tetrahydrofuran / 5 h

6: 78 percent / AlCl₃ / CH₂Cl₂ / 1 h / 20 °C

7: H₂ / Pd(OH)2 / methanol / 3 h

8: 0.162 g / methanol / 3 h

With lithium aluminium tetrahydride; dipyridinium dichromate; aluminium trichloride; hydrogen; magnesium; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; benzene; 1: Wittig olefination / 2: Reduction / 3: Reduction / 4: Oxidation / 5: Addition / 6: intramolecular Friedel-Crafts cyclization / 7: debenzylation / 8: Condensation;

DOI:10.1016/S0040-4020(99)01067-4

Reference yield:

(+)-(2R)-2-[bis(phenylmethyl)amino]-2-phenylethanol (193476-02-7) → cis-(1S,4S)-N-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine (267884-84-4)

Guidance literature:

Multi-step reaction with 9 steps

1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 0 °C

2: 2.62 g / benzene; CH₂Cl₂ / 15 h / 20 °C

3: 83 percent / Mg / 4 h

4: 76 percent / LiAlH₄ / tetrahydrofuran / 0 - 20 °C

5: 0.85 g / pyridinium dichromate / CH₂Cl₂ / 5 h / 20 °C

6: 1.0 g / tetrahydrofuran / 5 h

7: 78 percent / AlCl₃ / CH₂Cl₂ / 1 h / 20 °C

8: H₂ / Pd(OH)2 / methanol / 3 h

9: 0.162 g / methanol / 3 h

With lithium aluminium tetrahydride; dipyridinium dichromate; aluminium trichloride; oxalyl dichloride; hydrogen; magnesium; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; benzene; 1: Swern oxidation / 2: Wittig olefination / 3: Reduction / 4: Reduction / 5: Oxidation / 6: Addition / 7: intramolecular Friedel-Crafts cyclization / 8: debenzylation / 9: Condensation;

DOI:10.1016/S0040-4020(99)01067-4

Reference yield:

4-N,N-dibenzyl-4-phenyl-n-butanal → cis-(1S,4S)-N-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine (267884-84-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.0 g / tetrahydrofuran / 5 h

2: 78 percent / AlCl₃ / CH₂Cl₂ / 1 h / 20 °C

3: H₂ / Pd(OH)2 / methanol / 3 h

4: 0.162 g / methanol / 3 h

With aluminium trichloride; hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; 1: Addition / 2: intramolecular Friedel-Crafts cyclization / 3: debenzylation / 4: Condensation;

DOI:10.1016/S0040-4020(99)01067-4

upstream raw materials:

di-tert-butyl dicarbonate

norsertraline

D-dibenzylaminophenylglycinal

(+)-(2R)-2-[bis(phenylmethyl)amino]-2-phenylethanol

Downstream raw materials:

Sertraline

cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

Refernces

• 1、 Chandrasekhar,Venkat Reddy. "An expedient total synthesis of cis-(+)-sertraline from D-phenylglycine". . p. 1111 - 1114. Retrieved 2007/10/03.