(3aS,3bS,11bS)-10-iodo-1,2,3,3a,4,5,11b-octahydro-1-(phenylmethyl)-6H-dipyrrolo[1,2-a:3’,2’-c]-quinolin-6-one

Base Information

• Chemical Name: (3aS,3bS,11bS)-10-iodo-1,2,3,3a,4,5,11b-octahydro-1-(phenylmethyl)-6H-dipyrrolo[1,2-a:3’,2’-c]-quinolin-6-one
• CAS No.: 936114-56-6
• Molecular Formula: C₂₁H₂₁IN₂O
• Molecular Weight: 444.315

Synonyms:(3aS,3bS,11bS)-10-iodo-1,2,3,3a,4,5,11b-octahydro-1-(phenylmethyl)-6H-dipyrrolo[1,2-a:3’,2’-c]-quinolin-6-one

Chemical Property of (3aS,3bS,11bS)-10-iodo-1,2,3,3a,4,5,11b-octahydro-1-(phenylmethyl)-6H-dipyrrolo[1,2-a:3’,2’-c]-quinolin-6-one

Chemical Property:

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Technology Process of (3aS,3bS,11bS)-10-iodo-1,2,3,3a,4,5,11b-octahydro-1-(phenylmethyl)-6H-dipyrrolo[1,2-a:3’,2’-c]-quinolin-6-one

There total 10 articles about (3aS,3bS,11bS)-10-iodo-1,2,3,3a,4,5,11b-octahydro-1-(phenylmethyl)-6H-dipyrrolo[1,2-a:3’,2’-c]-quinolin-6-one 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: 71.0%

(5S)-5-ethenyl-1-[4-iodo-2-formylphenyl]-2-pyrrolidinol (936114-51-1) + N-benzyl glycine hydrochloride (7689-50-1) → 1-benzyl-10-iodo-1,2,3,3a,3b,4,5,11b-octahydro-dipyrrolo[1,2-a;3',2'-c]quinolin-6-one + (3aS,3bS,11bS)-10-iodo-1,2,3,3a,4,5,11b-octahydro-1-(phenylmethyl)-6H-dipyrrolo[1,2-a:3’,2’-c]-quinolin-6-one (936114-56-6)

Guidance literature:

With triethylamine; In toluene; at 120 ℃; for 23h; Inert atmosphere;

DOI:10.3987/COM-16-S(S)81

Reference yield:

methyl 5-nitro-2-[(5S)-5-{[(tert-butyl)dimethylsilyloxyethyl]}-2-oxo-1-pyrrolidinyl]benzoate (936114-10-2) → 1-benzyl-10-iodo-1,2,3,3a,3b,4,5,11b-octahydro-dipyrrolo[1,2-a;3',2'-c]quinolin-6-one + (3aS,3bS,11bS)-10-iodo-1,2,3,3a,4,5,11b-octahydro-1-(phenylmethyl)-6H-dipyrrolo[1,2-a:3’,2’-c]-quinolin-6-one (936114-56-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: hydrogen; palladium 10% on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr

2.1: n-Amyl nitrite; diiodomethane / acetonitrile / 22 h / 85 - 90 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C

4.1: o-nitrophenyl selenocyanate; tributylphosphine / tetrahydrofuran / 20 °C

4.2: 7 h / 0 - 20 °C

5.1: lithium borohydride; methanol / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere

6.1: manganese(IV) oxide / dichloromethane / 48 h / 25 °C / Inert atmosphere

7.1: triethylamine / toluene / 23 h / 120 °C / Inert atmosphere

With methanol; manganese(IV) oxide; lithium borohydride; diiodomethane; n-Amyl nitrite; tributylphosphine; palladium 10% on activated carbon; o-nitrophenyl selenocyanate; tetrabutyl ammonium fluoride; hydrogen; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;

DOI:10.3987/COM-16-S(S)81

Reference yield:

methyl 5-amino-2-[(5S)-5-{[(tert-butyl)dimethylsilyiloxyethyl]}-2-oxo-1-pyrrolidinyl]benzoate (936114-41-9) → 1-benzyl-10-iodo-1,2,3,3a,3b,4,5,11b-octahydro-dipyrrolo[1,2-a;3',2'-c]quinolin-6-one + (3aS,3bS,11bS)-10-iodo-1,2,3,3a,4,5,11b-octahydro-1-(phenylmethyl)-6H-dipyrrolo[1,2-a:3’,2’-c]-quinolin-6-one (936114-56-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-Amyl nitrite; diiodomethane / acetonitrile / 22 h / 85 - 90 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C

3.1: o-nitrophenyl selenocyanate; tributylphosphine / tetrahydrofuran / 20 °C

3.2: 7 h / 0 - 20 °C

4.1: lithium borohydride; methanol / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere

5.1: manganese(IV) oxide / dichloromethane / 48 h / 25 °C / Inert atmosphere

6.1: triethylamine / toluene / 23 h / 120 °C / Inert atmosphere

With methanol; manganese(IV) oxide; lithium borohydride; diiodomethane; n-Amyl nitrite; tributylphosphine; o-nitrophenyl selenocyanate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;

DOI:10.3987/COM-16-S(S)81

upstream raw materials:

(5S)-5-ethenyl-1-[4-iodo-2-formylphenyl]-2-pyrrolidinol

N-benzyl glycine hydrochloride

methyl 5-nitro-2-[(5S)-5-{[(tert-butyl)dimethylsilyloxyethyl]}-2-oxo-1-pyrrolidinyl]benzoate

methyl 5-amino-2-[(5S)-5-{[(tert-butyl)dimethylsilyiloxyethyl]}-2-oxo-1-pyrrolidinyl]benzoate

Downstream raw materials:

(3aS,4S,9bS)-8-iodo-2,3,3a,4,5,9b-hexahydro-1-(phenylmethyl)-1H-pyrrolo[3,2-c]quinoline-4-propanol

1-benzyl-4-(3-methanesulfonyloxy-propyl)-5-trifluoroacetyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-8-carboxylic acid methyl ester

methyl (3aS,4S,9bS)-2,3,3a,4,5,9b-hexahydro-5-(3-oxobutanoyl)-1-(phenylmethyl)-5-(trifluoroacetyl)-1H-pyrrolo[3,2-c]quinoline-8-carboxylate

(3aS,4S,9bS)-8-iodo-2,3,3a,4,5,9b-hexahydro-5-(3-oxobutanoyl)-1-(phenylmethyl)-1H-pyrrolo-[3,2-c]quinoline-4-propyl acetate

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