(S)-(-)-tert-Butyl-decahydro-3-isoquinolinecarboxamide

Base Information

• Chemical Name: (S)-(-)-tert-Butyl-decahydro-3-isoquinolinecarboxamide
• CAS No.: 136465-81-1
• Molecular Formula: C₁₄H₂₆N₂O
• Molecular Weight: 238.373
• Hs Code.: 29334900
• European Community (EC) Number: 420-380-5,603-964-6
• Mol file: 136465-81-1.mol

Synonyms:136465-81-1;MFCD00800360;(S)-N-t-Butyldecahydroisoquinoline-3-carboxamide;(S)-(-)-tert-Butyl-decahydro-3-isoquinolinecarboxamide;(3S,4aS,8aS)-N-tert-butyldecahydroisoquinoline-3-carboxamide

Chemical Property of (S)-(-)-tert-Butyl-decahydro-3-isoquinolinecarboxamide

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 1.18E-06mmHg at 25°C
• Melting Point: 112-115 °C(lit.)
• Refractive Index: 1.4590 (estimate)
• Boiling Point: 401.5 °C at 760 mmHg
• PKA: 15.65±0.20(Predicted)
• Flash Point: 146.7 °C
• PSA: 41.13000
• Density: 0.976 g/cm³
• LogP: 2.78910
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 238.204513457
• Heavy Atom Count: 17
• Complexity: 282

Purity/Quality:

99% ^*data from raw suppliers

(3S,4aS,8aS)-Decahydro-N-t-butyl-3-isoquinolinecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22-41-52/53
• Safety Statements: 24/25-61-39-26-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)NC(=O)C1CC2CCCCC2CN1
• Isomeric SMILES: CC(C)(C)NC(=O)[C@@H]1C[C@@H]2CCCC[C@H]2CN1
• Uses: Fragment present in various HIV-1 protease inhibitors currently in clinical trials for AIDS treatment. Intermediate in the production of HIV protease inhibitors

Technology Process of (S)-(-)-tert-Butyl-decahydro-3-isoquinolinecarboxamide

There total 11 articles about (S)-(-)-tert-Butyl-decahydro-3-isoquinolinecarboxamide 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: 85.0%

(S)-N-tert-butyl-1,2,3,4-tetrahydro-3-isoquinoline-carboxamide (149182-72-9) → (3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide (128019-40-9,149510-73-6,136465-81-1,168899-60-3)

Guidance literature:

With hydrogen; Rh/Al₂O₃; In ethyl acetate; at 150 ℃; under 112509 Torr;

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide (128019-40-9,149510-73-6,136465-81-1,168899-60-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / aq. HCl

2: COCl₂

4: 85 percent / H₂ / Rh/Alox / ethyl acetate / 150 °C / 112509 Torr

With hydrogenchloride; hydrogen; Rh/Al₂O₃; In ethyl acetate;

Reference yield:

L-Tic-OH (74163-81-8) → (3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide (128019-40-9,149510-73-6,136465-81-1,168899-60-3)

Guidance literature:

Multi-step reaction with 3 steps

1: COCl₂

3: 85 percent / H₂ / Rh/Alox / ethyl acetate / 150 °C / 112509 Torr

With hydrogen; Rh/Al₂O₃; In ethyl acetate;

upstream raw materials:

(3S,4aS,8aS)-3-tert-Butylcarbamoyl-octahydro-isoquinoline-2-carboxylic acid tert-butyl ester

tert-butylamine

(3S,4aS,8aS)-Decahydro-isoquinoline-3-carboxylic acid methyl ester

(S)-N-tert-butyl-1,2,3,4-tetrahydro-3-isoquinoline-carboxamide

Downstream raw materials:

N-tert-butyl-2-<2(R)-hydroxy-4-phenyl-3(S)-azidobutyl>decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide

(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-(phenylthio)butyl]decahydroisoquinoline-3-carboxamide

Refernces

• 1、 Trova, Michael P.,McGee Jr., Kevin F.. "Asymmetric synthesis of optically active decahydroisoquinolines useful in HIV-1 protease inhibitor synthesis". . p. 5951 - 5954. Retrieved 2007/10/02.
• 2、 Tucker, Thomas J.,Lumma, William C.,Payne, Linda S.,Wai, Jenny M.,Solms, S. Jane de,et al.. "A Series of Potent HIV-1 Protease Inhibitors Containing a Hydroxyethyl Secondary Amine Transition State Isostere: Synthesis, Enzyme Inhibition, and Antiviral Activity". . p. 2525 - 2533. Retrieved 2007/10/02.