(1S,2S,3S,4R)-3-(2-Benzyloxy-ethyl)-bicyclo[2.2.1]hept-2-ylamine

Base Information

• Chemical Name: (1S,2S,3S,4R)-3-(2-Benzyloxy-ethyl)-bicyclo[2.2.1]hept-2-ylamine
• CAS No.: 128217-57-2
• Molecular Formula: C₁₆H₂₃NO
• Molecular Weight: 245.365
• Mol file: 128217-57-2.mol

Synonyms:

Chemical Property of (1S,2S,3S,4R)-3-(2-Benzyloxy-ethyl)-bicyclo[2.2.1]hept-2-ylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3S,4R)-3-(2-Benzyloxy-ethyl)-bicyclo[2.2.1]hept-2-ylamine

There total 10 articles about (1S,2S,3S,4R)-3-(2-Benzyloxy-ethyl)-bicyclo[2.2.1]hept-2-ylamine 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:

(4S)-3-(((3'R,4'R,5'S,6'S)-5'-(2-(Benzyloxy)ethyl)bicyclo<2.2.1>hepten-4'-yl)carbonyl)-4-(phenylmethyl)-2-oxazolidinone (128300-77-6) → (1S,2S,3S,4R)-3-(2-Benzyloxy-ethyl)-bicyclo[2.2.1]hept-2-ylamine (128217-57-2)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 5percent Pt / C / ethyl acetate / 2 h / 1861.7 Torr / Ambient temperature

2: 87.9 percent / 30percent H₂O₂, LiOH*H₂O / tetrahydrofuran; H₂O / 10 h / 3 °C

With lithium hydroxide; hydrogen; dihydrogen peroxide; platinum on activated charcoal; In tetrahydrofuran; water; ethyl acetate;

DOI:10.1021/jo00304a019

Reference yield:

2-phenyl-1,3-dioxane (772-01-0) → (1S,2S,3S,4R)-3-(2-Benzyloxy-ethyl)-bicyclo[2.2.1]hept-2-ylamine (128217-57-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 89 percent / 1.)diisobutylaluminum hydride, 2.)methanol / toluene / Ambient temperature

2: oxalyl chloride - DMSO, Et₃N / CH₂Cl₂ / 0.75 h / -70 - -65 °C

3: 181.2 g / CH₂Cl₂ / 1.)-70 -> -65 deg C, 15 min., 2.)r.t., 4 h

4: 1N NaOH / tetrahydrofuran / 5 h / Ambient temperature

6: Et₂AlCl / CH₂Cl₂ / 5 h / -78 °C

7: 87.9 percent / 30percent H₂O₂, LiOH*H₂O / tetrahydrofuran; H₂O / 10 h / 3 °C

With methanol; lithium hydroxide; sodium hydroxide; oxalyl dichloride; dihydrogen peroxide; diethylaluminium chloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1021/jo00304a019

Reference yield:

3-benzyloxypropan-1-ol (4799-68-2) → (1S,2S,3S,4R)-3-(2-Benzyloxy-ethyl)-bicyclo[2.2.1]hept-2-ylamine (128217-57-2)

Guidance literature:

Multi-step reaction with 7 steps

1: oxalyl chloride - DMSO, Et₃N / CH₂Cl₂ / 0.75 h / -70 - -65 °C

2: 181.2 g / CH₂Cl₂ / 1.)-70 -> -65 deg C, 15 min., 2.)r.t., 4 h

3: 1N NaOH / tetrahydrofuran / 5 h / Ambient temperature

5: Et₂AlCl / CH₂Cl₂ / 5 h / -78 °C

6: 87.9 percent / 30percent H₂O₂, LiOH*H₂O / tetrahydrofuran; H₂O / 10 h / 3 °C

With lithium hydroxide; sodium hydroxide; oxalyl dichloride; dihydrogen peroxide; diethylaluminium chloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00304a019

upstream raw materials:

chloroformic acid ethyl ester

(3'R,4'R,5'S,6'S)-5-(2-(Benzyloxy)ethyl)-4'-carboxybicyclo<2.2.1>heptane

2-phenyl-1,3-dioxane

3-benzyloxypropan-1-ol

Downstream raw materials:

(3'R,4'R,5'S,6'S)-5-(2-(Benzyloxy)ethyl)-4'-benzenesulfonamidobicyclo<2.2.1>heptane

(3'R,4'R,5'S,6'S)-5'-(2-Hydroxyethyl)-4'-benzenesulfonamidobicyclo<2.2.1>heptane

(3'R,4'R,5'S,6'S)-5'-(Formylmethyl)-4'-benzenesulfonamidobicyclo<2.2.1>heptane

(Z)-7-((1R,2S,3R,4S)-3-Benzenesulfonylamino-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid