1,1-dimethylethyl (+/-)-6-ethyl-2-(phenylmethyl)-2-azabicyclo<4.2.0>octane-8-carboxylate

Base Information

• Chemical Name: 1,1-dimethylethyl (+/-)-6-ethyl-2-(phenylmethyl)-2-azabicyclo<4.2.0>octane-8-carboxylate
• CAS No.: 124286-80-2
• Molecular Formula: C₂₁H₃₁NO₂
• Molecular Weight: 329.483
• Mol file: 124286-80-2.mol

Synonyms:1,1-dimethylethyl (+/-)-6-ethyl-2-(phenylmethyl)-2-azabicyclo<4.2.0>octane-8-carboxylate

Chemical Property of 1,1-dimethylethyl (+/-)-6-ethyl-2-(phenylmethyl)-2-azabicyclo<4.2.0>octane-8-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1-dimethylethyl (+/-)-6-ethyl-2-(phenylmethyl)-2-azabicyclo<4.2.0>octane-8-carboxylate

There total 1 articles about 1,1-dimethylethyl (+/-)-6-ethyl-2-(phenylmethyl)-2-azabicyclo<4.2.0>octane-8-carboxylate 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: 31.0%

1-(phenylmethyl)-3-ethyl-1,4,5,6-tetrahydropyridine (19716-82-6) + tert-Butyl acrylate (1663-39-4,25232-27-3) → 1,1-dimethylethyl (+/-)-6-ethyl-2-(phenylmethyl)-2-azabicyclo<4.2.0>octane-8-carboxylate (124286-80-2)

Guidance literature:

In acetonitrile; at 105 ℃;

DOI:10.1021/jo00290a006

Reference yield:

1,1-dimethylethyl (+/-)-6-ethyl-2-(phenylmethyl)-2-azabicyclo<4.2.0>octane-8-carboxylate (124286-80-2) → cis-(+/-)-1-(3-chlorophenyl)-7a-ethyl-6,7,7a,8,9,9b-hexahydro-3H-cyclopentaquinolizin-2(5H)-one (124286-88-0)

Guidance literature:

Multi-step reaction with 7 steps

1: methanol / Heating

2: 65 percent / t-BuOK / toluene / 12 h / 65 °C

3: 66 percent / 20percent H₂SO₄ / 0.75 h / Heating

4: 78 percent / 2-naphthalenesulfonic acid / toluene / 15 h / Heating

5: 98 percent / H₂, conc. HCl / 10percent Pd/C / methanol / 16 h

6: 73 percent / diisopropylethylamine / acetonitrile / 0.67 h / Heating

7: 59 percent / 1.4 N HCl / 1.75 h / Heating

With hydrogenchloride; naphthalene-2-sulfonate; sulfuric acid; potassium tert-butylate; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; toluene; acetonitrile;

DOI:10.1021/jo00290a006

Reference yield:

1,1-dimethylethyl (+/-)-6-ethyl-2-(phenylmethyl)-2-azabicyclo<4.2.0>octane-8-carboxylate (124286-80-2) → cis-(+/-)-1-(3-chlorophenyl)-3-(4'a-ethylhexahydrospiro<1,3-dioxolane-2,7'-<7H-1>pyrindin>-1'(2'H)-yl)-2-propanone (124286-87-9)

Guidance literature:

Multi-step reaction with 6 steps

1: methanol / Heating

2: 65 percent / t-BuOK / toluene / 12 h / 65 °C

3: 66 percent / 20percent H₂SO₄ / 0.75 h / Heating

4: 78 percent / 2-naphthalenesulfonic acid / toluene / 15 h / Heating

5: 98 percent / H₂, conc. HCl / 10percent Pd/C / methanol / 16 h

6: 73 percent / diisopropylethylamine / acetonitrile / 0.67 h / Heating

With hydrogenchloride; naphthalene-2-sulfonate; sulfuric acid; potassium tert-butylate; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; toluene; acetonitrile;

DOI:10.1021/jo00290a006

upstream raw materials:

1-(phenylmethyl)-3-ethyl-1,4,5,6-tetrahydropyridine

tert-Butyl acrylate

Downstream raw materials:

1,1-dimethylethyl (+/-)-3-(2'-cyano-3'-ethyl-1'-(phenylmethyl)hexahydropyridin-3'-yl)propanoate

cis-(+/-)-4a-ethyloctahydro-1-(phenylmethyl)-7H-1-pyridin-7-one

(+/-)-4a-ethyloctahydro-8-(phenylmethyl)-2H-pyrano<2,3-b>pyridin-2-one

cis-(+/-)-4a-ethyloctahydro-1-(phenylmethyl)-7H-1-pyridin-7-one ethylene ketal