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

Base Information

• Chemical Name: (1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-(S)-phenylmethanol
• CAS No.: 234451-89-9
• Molecular Formula: C₂₁H₂₅NO
• Molecular Weight: 307.436
• Mol file: 234451-89-9.mol

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

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

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)-phenylmethanol

There total 7 articles about (1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-(S)-phenylmethanol 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: 98.0%

phenylmagnesium bromide + (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)-phenylmethanol (234451-89-9)

Guidance literature:

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

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

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

Reference yield: 84.0%

phenylmagnesium bromide (100-58-3) + (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)-phenylmethanol (234451-89-9)

Guidance literature:

With cerium(III) chloride; In tetrahydrofuran; at -78 - 20 ℃; for 20h; Inert atmosphere;

DOI:10.1002/ejoc.201900308

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)-phenylmethanol (234451-89-9)

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: cerium chloride / diethyl ether; tetrahydrofuran / 1 h / -78 °C

4.2: 98 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C

With lithium aluminium tetrahydride; cerium(III) chloride; oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 1.1: Catalytic hydrogenation / 2.1: Reduction / 3.1: Oxidation / 4.1: transmetallation / 4.2: Addition;

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

upstream raw materials:

(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

(1S,3R,4R)-2-[(S)-1-phenylethyl]-3-hydroxymethyl-2-azabicyclo[2.2.1]heptane

Downstream raw materials:

(1S,3R,4R)-2-Azabicyclo[2.2.1]heptane-3-(S)-phenylmethanol

Refernces

• 1、 Brandt, Peter,Hedberg, Christian,Lawonn, Klaus,Pinho, Pedro,Andersson, Pher G.. "A theoretical and experimental study of the asymmetric addition of dialkylzinc to N-(diphenylphosphinoyl)benzalimine". . p. 1692 - 1699. Retrieved 2007/10/03.