(1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-(S)-isopropylmethanol

Base Information

• Chemical Name: (1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-(S)-isopropylmethanol
• CAS No.: 234451-91-3
• Molecular Formula: C₁₈H₂₇NO
• Molecular Weight: 273.418
• Mol file: 234451-91-3.mol

Synonyms:(1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-(S)-isopropylmethanol

Chemical Property of (1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-(S)-isopropylmethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-(S)-isopropylmethanol

There total 4 articles about (1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-(S)-isopropylmethanol 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: 78.0%

isopropyl bromide (75-26-3) + (1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-carboxaldehyde (215674-17-2) → (1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-(S)-isopropylmethanol (234451-91-3)

Guidance literature:

isopropyl bromide; With magnesium; In tetrahydrofuran;

With cerium(III) chloride; In tetrahydrofuran; at -78 ℃; for 1h;

(1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-carboxaldehyde; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1002/(SICI)1521-3765(19990604)5:6<1692::AID-CHEM1692>3.0.CO;2-M

Reference yield:

(1R,3R,4S)-2-<(1S)-phenylethyl>-2-aza-bicyclo<2.2.1>hept-5-ene-3-carboxylic acid ethyl ester (223505-12-2) → (1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-(S)-isopropylmethanol (234451-91-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 92 percent / H₂ / 10 percent Pd/C / ethanol / 20 °C / 760 Torr

2.1: LiAlH₄ / tetrahydrofuran / 20 °C

3.1: 92 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: Mg / tetrahydrofuran

4.2: cerium chloride / tetrahydrofuran / 1 h / -78 °C

4.3: 78 percent / tetrahydrofuran / -78 - 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; magnesium; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; 1.1: Catalytic hydrogenation / 2.1: Reduction / 3.1: Oxidation / 4.1: Metallation / 4.2: transmetallation / 4.3: Addition;

DOI:10.1002/(SICI)1521-3765(19990604)5:6<1692::AID-CHEM1692>3.0.CO;2-M

Reference yield:

(1S,3R,4R)-2-<(1S)-phenylethyl>-2-aza-bicyclo<2.2.1>heptane-3-carboxylic acid ethyl ester (223473-32-3) → (1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-(S)-isopropylmethanol (234451-91-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiAlH₄ / tetrahydrofuran / 20 °C

2.1: 92 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: Mg / tetrahydrofuran

3.2: cerium chloride / tetrahydrofuran / 1 h / -78 °C

3.3: 78 percent / tetrahydrofuran / -78 - 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Reduction / 2.1: Oxidation / 3.1: Metallation / 3.2: transmetallation / 3.3: Addition;

DOI:10.1002/(SICI)1521-3765(19990604)5:6<1692::AID-CHEM1692>3.0.CO;2-M

upstream raw materials:

isopropyl bromide

(1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-carboxaldehyde

(1R,3R,4S)-2-<(1S)-phenylethyl>-2-aza-bicyclo<2.2.1>hept-5-ene-3-carboxylic acid ethyl ester

(1S,3R,4R)-2-<(1S)-phenylethyl>-2-aza-bicyclo<2.2.1>heptane-3-carboxylic acid ethyl ester

Refernces