N-methyl-N-<(1S)-1-(4-nitrophenyl)-2-(1-pyrrolidinyl)ethyl>-(S)-α-acetoxyphenylacetamide

Base Information

• Chemical Name: N-methyl-N-<(1S)-1-(4-nitrophenyl)-2-(1-pyrrolidinyl)ethyl>-(S)-α-acetoxyphenylacetamide
• CAS No.: 157948-04-4
• Molecular Formula: C₂₃H₂₇N₃O₅
• Molecular Weight: 425.484
• Mol file: 157948-04-4.mol

Synonyms:N-methyl-N-<(1S)-1-(4-nitrophenyl)-2-(1-pyrrolidinyl)ethyl>-(S)-α-acetoxyphenylacetamide

Chemical Property of N-methyl-N-<(1S)-1-(4-nitrophenyl)-2-(1-pyrrolidinyl)ethyl>-(S)-α-acetoxyphenylacetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-methyl-N-<(1S)-1-(4-nitrophenyl)-2-(1-pyrrolidinyl)ethyl>-(S)-α-acetoxyphenylacetamide

There total 6 articles about N-methyl-N-<(1S)-1-(4-nitrophenyl)-2-(1-pyrrolidinyl)ethyl>-(S)-α-acetoxyphenylacetamide 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: 30.0%

(S)-2-chloro-2-oxo-1-phenylethyl acetate (51019-44-4) + (+/-)-1-<2-(methylamino)-2-(4-nitrophenyl)ethyl>pyrrolidine (157948-03-3) → N-methyl-N-<(1R)-1-(4-nitrophenyl)-2-(1-pyrrolidinyl)ethyl>-(S)-α-acetoxyphenylacetamide + N-methyl-N-<(1S)-1-(4-nitrophenyl)-2-(1-pyrrolidinyl)ethyl>-(S)-α-acetoxyphenylacetamide (157948-04-4)

Guidance literature:

With pyridine; In dichloromethane; at 5 ℃; for 16h;

DOI:10.1021/jm00044a006

Reference yield:

α-bromomethyl p-nitrophenyl ketoxime (14181-73-8) → N-methyl-N-<(1S)-1-(4-nitrophenyl)-2-(1-pyrrolidinyl)ethyl>-(S)-α-acetoxyphenylacetamide (157948-04-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / CH₂Cl₂ / 4 h / Ambient temperature

2: 84 percent / BH₃*THF / tetrahydrofuran / 24 h / Heating

3: 87 percent / 24 h / Ambient temperature

4: 81 percent / BH₃*dimethyl sulfide / tetrahydrofuran / 2 h / Heating

5: 30 percent / pyridine / CH₂Cl₂ / 16 h / 5 °C

With pyridine; borane-THF; dimethylsulfide borane complex; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm00044a006

Reference yield:

(S)-acetylmandelic acid (7322-88-5) → N-methyl-N-<(1S)-1-(4-nitrophenyl)-2-(1-pyrrolidinyl)ethyl>-(S)-α-acetoxyphenylacetamide (157948-04-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / oxalyl chloride / CH₂Cl₂ / 10 h / Ambient temperature

2: 30 percent / pyridine / CH₂Cl₂ / 16 h / 5 °C

With pyridine; oxalyl dichloride; In dichloromethane;

DOI:10.1021/jm00044a006

upstream raw materials:

(S)-2-chloro-2-oxo-1-phenylethyl acetate

(+/-)-1-<2-(methylamino)-2-(4-nitrophenyl)ethyl>pyrrolidine

α-bromomethyl p-nitrophenyl ketoxime

(S)-acetylmandelic acid

Downstream raw materials:

N-methyl-N-<(1S)-1-(4-nitrophenyl)-2-(1-pyrrolidinyl)ethyl>-3,4-dichlorophenylacetamide

N-methyl-N-<(1S)-1-(4-aminophenyl)-2-(1-pyrrolidinyl)ethyl>-3,4-dichlorophenylacetamide

1-<(2S)-2-(4-nitrophenyl)-2-(methylamino)ethyl>pyrrolidine