cis-(+/-)-1-(3-chlorophenyl)-3-(4'a-ethylhexahydrospiro<1,3-dioxolane-2,7'-<7H-1>pyrindin>-1'(2'H)-yl)-2-propanone

Base Information

• Chemical Name: cis-(+/-)-1-(3-chlorophenyl)-3-(4'a-ethylhexahydrospiro<1,3-dioxolane-2,7'-<7H-1>pyrindin>-1'(2'H)-yl)-2-propanone
• CAS No.: 124286-87-9
• Molecular Formula: C₂₁H₂₈ClNO₃
• Molecular Weight: 377.911
• Mol file: 124286-87-9.mol

Synonyms:cis-(+/-)-1-(3-chlorophenyl)-3-(4'a-ethylhexahydrospiro<1,3-dioxolane-2,7'-<7H-1>pyrindin>-1'(2'H)-yl)-2-propanone

Chemical Property of cis-(+/-)-1-(3-chlorophenyl)-3-(4'a-ethylhexahydrospiro<1,3-dioxolane-2,7'-<7H-1>pyrindin>-1'(2'H)-yl)-2-propanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-(+/-)-1-(3-chlorophenyl)-3-(4'a-ethylhexahydrospiro<1,3-dioxolane-2,7'-<7H-1>pyrindin>-1'(2'H)-yl)-2-propanone

There total 10 articles about cis-(+/-)-1-(3-chlorophenyl)-3-(4'a-ethylhexahydrospiro<1,3-dioxolane-2,7'-<7H-1>pyrindin>-1'(2'H)-yl)-2-propanone 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: 73.0%

1-chloro-3-(3'-chlorophenyl)-2-propanone (24253-17-6) + cis-(+/-)-4a-ethyloctahydro-7H-1-pyridin-7-one ethylene ketal (124286-86-8) → 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:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 0.666667h; Heating;

DOI:10.1021/jo00290a006

Reference yield:

1-(phenylmethyl)-3-ethyl-1,4,5,6-tetrahydropyridine (19716-82-6) → 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 7 steps

1: 31 percent / acetonitrile / 105 °C

2: methanol / Heating

3: 65 percent / t-BuOK / toluene / 12 h / 65 °C

4: 66 percent / 20percent H₂SO₄ / 0.75 h / Heating

5: 78 percent / 2-naphthalenesulfonic acid / toluene / 15 h / Heating

6: 98 percent / H₂, conc. HCl / 10percent Pd/C / methanol / 16 h

7: 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

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-chloro-3-(3'-chlorophenyl)-2-propanone

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

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

3-chlorophenylacetic acid

Downstream raw materials:

cis-(+/-)-1-(3-chlorophenyl)-7a-ethyl-6,7,7a,8,9,9b-hexahydro-3H-cyclopentaquinolizin-2(5H)-one