136465-81-1

Basic information

• Product Name: N-(tert-Butyl)decahydroisoquinoline-3-carboxamide
• Synonyms: N-(TERT-BUTYL)DECAHYDROISOQUINOLINE-3-CARBOXAMIDE;(S)-T-BUTYL-DECAHYDRO-3-ISOQUINOLINE CARBOXAMIDE;(S)-(-)-TERT-BUTYL-DECAHYDRO-3-ISOQUINOLINECARBOXAMIDE;(S)-TERT-BUTYL DECAHYDRO-3-ISOQUINOLINECARBOXAMIDE;TIMTEC-BB SBB009946;(3S,4aS,8aS)-N-(1,1-DiMethylethyl)decahydro-3-isoquinolinecarboxaMide;(3S,4aS,8aS)-Decahydroisoquinoline-3-carboxylic acid tert-butylaMide;3-IsoquinolinecarboxaMide, N-(1,1-diMethylethyl)decahydro-, [3S-(3α,4aβ,8aβ)]-
• CAS NO: 136465-81-1
• Molecular Formula: C₁₄H₂₆N₂O
• Molecular Weight: 238.37
• EINECS: 420-380-5
• Product Categories: Building Blocks for HIV Protease InhibitorsChiral Building Blocks;Cell Signaling Enzymes;Heterocyclic Building Blocks;HIV Protease Reagents&Envelope Proteins;Isoquinolines;Aromatics;Chiral Reagents;Nelfinavir
• Mol File: 136465-81-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 112-115 °C(lit.)
• Boiling Point: 380.97°C (rough estimate)
• Flash Point: 146.7 °C
• Appearance: White solid
• Density: 1.09
• Vapor Pressure: 1.18E-06mmHg at 25°C
• Refractive Index: 1.4590 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 15.65±0.20(Predicted)
• CAS DataBase Reference: N-(tert-Butyl)decahydroisoquinoline-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-Butyl)decahydroisoquinoline-3-carboxamide(136465-81-1)
• EPA Substance Registry System: N-(tert-Butyl)decahydroisoquinoline-3-carboxamide(136465-81-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-41-52/53
• Safety Statements: 24/25-61-39-26-22
• WGK Germany: 3
• Hazardous Substances Data: 136465-81-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 136465-81-1 differently. You can refer to the following data:
1. Fragment present in various HIV-1 protease inhibitors currently in clinical trials for AIDS treatment.
2. Intermediate in the production of HIV protease inhibitors

InChI:InChI=1/C14H26N2O/c1-14(2,3)16-13(17)12-8-10-6-4-5-7-11(10)9-15-12/h10-12,15H,4-9H2,1-3H3,(H,16,17)/p+1/t10-,11-,12-/m0/s1

Upstream product

• 143978-60-3 (3S,4aS,8aS)-3-tert-Butylcarbamoyl-octahydro-isoquinoline-2-carboxylic acid tert-butyl ester 
• 75-64-9 tert-butylamine 
• 149510-69-0 (3S,4aS,8aS)-Decahydro-isoquinoline-3-carboxylic acid methyl ester 
• 149182-72-9 (S)-N-tert-butyl-1,2,3,4-tetrahydro-3-isoquinoline-carboxamide 
• 63-91-2 L-phenylalanine 
• 115238-59-0 (4aS,8aS)-N-Boc-decahydroisoquinolin-3(S)-carboxylic acid 
• 1064005-84-0 (S)-1,2,3,4-Tetrahydro-isoquinoline-3-carbonyl chloride 
• 149182-71-8 benzyl 3(S)-(t-butylcarbamoyl)-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate 
• 79261-58-8 (S)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester 
• 74163-81-8 L-Tic-OH 

Downstream Products

• 159989-64-7 nelfinavir 
• 870073-16-8 C₂₉H₄₂⁽²⁾H₅N₃O₄ 
• 1025935-06-1 (3S,4aS,8aS)-2-[(2S,3S)-3-Hydroxy-2-(3-hydroxy-2-methyl-benzoylamino)-4-phenylsulfanyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide 
• 188936-07-4 (3S,4aS,8aS)-N-tert-butyl-2-((R)-2-hydroxy-2-((S)-2-(3-hydroxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethyl)-decahydroisoquinoline-3-carboxamide 
• 1185258-46-1 (-)-(R)-3-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-2-hydroxypropyl 4-methylbenzenesulfonate 
• 1208246-89-2 (3S,4aS,8aS)-2-((2R,3S)-3-azido-2-hydroxy-4-(4-phenylthiophen-2-yl)butyl)-N-tertbutyldecahydroisoquinoline-3-carboxamide 
• 1208246-88-1 (3S,4aS,8aS)-2-((2R,3R)-3-azido-2-hydroxy-3-(4-phenylthiophen-2-yl)propyl)-N-tertbutyldecahydroisoquinoline-3-carboxamide 
• 1014685-52-9 (-)-(3S,4aS,8aS,2'S,3'S)-2-[2',3'-epoxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide 
• 1014685-45-0 (-)-(3S,4aS,8aS,2'R,3'R)-2-[2',3'-epoxy-4'-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamide 
• 159878-05-4 (3S,4AS,8AS)-2-((2R,3R)-3-amino-2-hydroxy-4-phenylthiobutyl)-decahydroisoquinoline-3-carboxylic acid t-butylamide 
• 159878-04-3 (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-(phenylthio)butyl]decahydroisoquinoline-3-carboxamide 
• 150331-80-9 (3S,4aS,8aS)-2-[(2R,3S)-3-((S)-2-Azido-2-(R)-tetrahydro-furan-3-yl-acetylamino)-2-hydroxy-4-phenyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide 

Relevant articles and documents

Synthesis of the HIV-proteinase inhibitor Saquinavir: A challenge for process research

The task of process research, namely developing efficient, economically and technically as well as ecologically feasible syntheses in time, is demonstrated on the HIV-proteinase inhibitor Saquinavir (1), a complex molecule comprising six stereo-centres. Based on the first 26-step research synthesis furnishing a 10% overall yield, process research established a new, short 11-step synthesis affording a 50% overall yield.

Towards the synthesis of HIV-protease inhibitors. Synthesis optically pure 3-carboxyl-decahydroisoquinolines

The synthesis of optically pure decahydroisoquinoline 1, a component of HIV-protease inhibitors, was accomplished in 30-33% overall yield from the readily available optically pure monoacid 4.