(1S,1'R,1''R,2S,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]-1,2,3,4-tetrahydro-1-naphthalinol

Base Information

• Chemical Name: (1S,1'R,1''R,2S,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]-1,2,3,4-tetrahydro-1-naphthalinol
• CAS No.: 253609-35-7
• Molecular Formula: C₂₄H₂₉NO
• Molecular Weight: 347.5
• Mol file: 253609-35-7.mol

Synonyms:(1S,1'R,1''R,2S,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]-1,2,3,4-tetrahydro-1-naphthalinol

Chemical Property of (1S,1'R,1''R,2S,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]-1,2,3,4-tetrahydro-1-naphthalinol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,1'R,1''R,2S,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]-1,2,3,4-tetrahydro-1-naphthalinol

There total 5 articles about (1S,1'R,1''R,2S,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]-1,2,3,4-tetrahydro-1-naphthalinol 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: 55.0%

(1'R,1''R,2S,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]-1,2,3,4-tetrahydro-1-naphthalinone (253609-31-3) → (1S,1'R,1''R,2S,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]-1,2,3,4-tetrahydro-1-naphthalinol (253609-35-7) + (1R,1'R,1''R,2S,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]-1,2,3,4-tetrahydro-1-naphthalinol (253609-34-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -70 ℃; for 1.5h;

DOI:10.1016/S0957-4166(99)00342-0

Reference yield:

(3aR,6aR)-octahydrocyclopentapyrrole (156473-27-7) → (1S,1'R,1''R,2S,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]-1,2,3,4-tetrahydro-1-naphthalinol (253609-35-7)

Guidance literature:

Multi-step reaction with 4 steps

1: NaI; Et₃N / acetonitrile / 1 h

2: NaI; Et₃N / acetonitrile / 1.5 h

3: 78 percent / acetonitrile / 2 h / 20 °C

4: 32 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / -70 °C

With lithium aluminium tetrahydride; triethylamine; sodium iodide; In tetrahydrofuran; acetonitrile; 1: silylation / 2: Condensation / 3: aminoalkylation; Mannich reaction / 4: Reduction;

DOI:10.1016/S0957-4166(99)00342-0

Reference yield:

1-(3,4-dihydro-1-naphthalenyl)pyrrolidine (7007-34-3) → (1S,1'R,1''R,2S,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]-1,2,3,4-tetrahydro-1-naphthalinol (253609-35-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / acetonitrile / 2 h / 20 °C

2: 32 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / -70 °C

With lithium aluminium tetrahydride; In tetrahydrofuran; acetonitrile; 1: aminoalkylation; Mannich reaction / 2: Reduction;

DOI:10.1016/S0957-4166(99)00342-0

upstream raw materials:

(1'R,1''R,2S,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]-1,2,3,4-tetrahydro-1-naphthalinone

(3aR,6aR)-octahydrocyclopentapyrrole

1-(3,4-dihydro-1-naphthalenyl)pyrrolidine

Downstream raw materials:

(S)-2-benzyl-1-tetralone

trans-2-benzyl-1,2,3,4-tetrahydronaphthalen-1-ol