(3S,4R)-4-(iodomethyl)-3-methyl-1-(phenylmethoxy)-3-[(1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)methyl]-2-pyrrolidinone

Base Information

• Chemical Name: (3S,4R)-4-(iodomethyl)-3-methyl-1-(phenylmethoxy)-3-[(1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)methyl]-2-pyrrolidinone
• CAS No.: 1345966-29-1
• Molecular Formula: C₂₀H₁₇F₁₁INO₂
• Molecular Weight: 639.247
• Mol file: 1345966-29-1.mol

Synonyms:(3S,4R)-4-(iodomethyl)-3-methyl-1-(phenylmethoxy)-3-[(1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)methyl]-2-pyrrolidinone

Chemical Property of (3S,4R)-4-(iodomethyl)-3-methyl-1-(phenylmethoxy)-3-[(1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)methyl]-2-pyrrolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-4-(iodomethyl)-3-methyl-1-(phenylmethoxy)-3-[(1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)methyl]-2-pyrrolidinone

There total 6 articles about (3S,4R)-4-(iodomethyl)-3-methyl-1-(phenylmethoxy)-3-[(1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)methyl]-2-pyrrolidinone 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: 50.0%

N-(phenylmethoxy)-2-methyl-N-(2-propen-1-yl)-2-propenamide (914498-71-8) + iodoundecafluorocyclohexane (355-69-1) → (3S,4R)-4-(iodomethyl)-3-methyl-1-(phenylmethoxy)-3-[(1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)methyl]-2-pyrrolidinone (1345966-29-1) + cis-3-(iodomethyl)-3-methyl-1-(phenylmethoxy)-4-[(1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)methyl]-2-pyrrolidinone

Guidance literature:

N-(phenylmethoxy)-2-methyl-N-(2-propen-1-yl)-2-propenamide; With (3aR,3a’R,8aS,8a’S)-2,2’-(cyclopropane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]-oxazole); zinc trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

iodoundecafluorocyclohexane; With triethyl borane; In hexane; dichloromethane; at -78 ℃; for 72h; enantioselective reaction;

DOI:10.1021/jo3015227

Reference yield:

N-(phenylmethoxy)-2-methyl-N-(2-propen-1-yl)-2-propenamide (914498-71-8) + iodoundecafluorocyclohexane (355-69-1) → (3S,4R)-4-(iodomethyl)-3-methyl-1-(phenylmethoxy)-3-[(1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)methyl]-2-pyrrolidinone (1345966-29-1) + (3S,4S)-4-(iodomethyl)-3-methyl-1-(phenylmethoxy)-3-[(1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)methyl]-2-pyrrolidinone + cis-3-(iodomethyl)-3-methyl-1-(phenylmethoxy)-4-[(1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)methyl]-2-pyrrolidinone

Guidance literature:

N-(phenylmethoxy)-2-methyl-N-(2-propen-1-yl)-2-propenamide; With (3aR,3a’R,8aS,8a’S)-2,2’-(cyclopropane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]-oxazole); zinc trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

iodoundecafluorocyclohexane; With triethyl borane; In hexane; dichloromethane; at -78 ℃; for 2.5h; Overall yield = 66 %; regioselective reaction;

DOI:10.1021/jo3015227

Reference yield:

N-allyl-O-benzylhydroxylamine (122149-19-3) → (3S,4R)-4-(iodomethyl)-3-methyl-1-(phenylmethoxy)-3-[(1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)methyl]-2-pyrrolidinone (1345966-29-1) + cis-3-(iodomethyl)-3-methyl-1-(phenylmethoxy)-4-[(1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)methyl]-2-pyrrolidinone

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: (3aR,3a’R,8aS,8a’S)-2,2’-(cyclopropane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]-oxazole); zinc trifluoromethanesulfonate / dichloromethane / 1 h / 20 °C / Inert atmosphere

2.2: 2.5 h / -78 °C

With (3aR,3a’R,8aS,8a’S)-2,2’-(cyclopropane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]-oxazole); zinc trifluoromethanesulfonate; triethylamine; In dichloromethane;

DOI:10.1021/jo3015227

upstream raw materials:

N-(phenylmethoxy)-2-methyl-N-(2-propen-1-yl)-2-propenamide

iodoundecafluorocyclohexane

N-allyl-O-benzylhydroxylamine

N-(phenylmethoxy)-N-2-propenylcarbamic acid 1,1-dimethylethyl ester