(2S,3S,4R)-N-benzyl-3,4-(isopropylidenedioxy)-2-vinyl-pyrrolidine

Base Information

• Chemical Name: (2S,3S,4R)-N-benzyl-3,4-(isopropylidenedioxy)-2-vinyl-pyrrolidine
• CAS No.: 851390-79-9
• Molecular Formula: C₁₆H₂₁NO₂
• Molecular Weight: 259.348
• Mol file: 851390-79-9.mol

Synonyms:(2S,3S,4R)-N-benzyl-3,4-(isopropylidenedioxy)-2-vinyl-pyrrolidine

Chemical Property of (2S,3S,4R)-N-benzyl-3,4-(isopropylidenedioxy)-2-vinyl-pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-N-benzyl-3,4-(isopropylidenedioxy)-2-vinyl-pyrrolidine

There total 2 articles about (2S,3S,4R)-N-benzyl-3,4-(isopropylidenedioxy)-2-vinyl-pyrrolidine 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: 89.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (2S,3S,4R)-N-benzyl-2-formyl-3,4-(isopropylidenedioxy)pyrrolidine (132430-78-5) → (2S,3S,4R)-N-benzyl-3,4-(isopropylidenedioxy)-2-vinyl-pyrrolidine (851390-79-9)

Guidance literature:

Methyltriphenylphosphonium bromide; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

(2S,3S,4R)-N-benzyl-2-formyl-3,4-(isopropylidenedioxy)pyrrolidine; In tetrahydrofuran; toluene; at -78 ℃; for 12h;

DOI:10.1055/s-2005-861792

Reference yield:

Benzyl-[1-((3aS,4R,6aR)-5-benzyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-meth-(E)-ylidene]-amine → (2S,3S,4R)-N-benzyl-3,4-(isopropylidenedioxy)-2-vinyl-pyrrolidine (851390-79-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 224 mg / silica gel / hexane; ethyl acetate

2.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

2.2: 89 percent / toluene; tetrahydrofuran / 12 h / -78 °C

With silica gel; potassium hexamethylsilazane; In tetrahydrofuran; hexane; ethyl acetate; toluene;

DOI:10.1055/s-2005-861792

Reference yield: 76.0%

(2S,3S,4R)-N-benzyl-3,4-(isopropylidenedioxy)-2-vinyl-pyrrolidine (851390-79-9) → (S)-1-((3aS,4R,6aR)-5-benzyl-2,2-dimethyltetrahydro-4H-[1,3] dioxolo[4,5-c]pyrrol-4-yl)ethane-1,2-diol (851390-80-2)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; In 1,4-dioxane; tert-butyl alcohol; at 60 ℃; for 24h;

DOI:10.1055/s-2005-861792

upstream raw materials:

Methyltriphenylphosphonium bromide

(2S,3S,4R)-N-benzyl-2-formyl-3,4-(isopropylidenedioxy)pyrrolidine

Downstream raw materials:

(S)-1-((3aS,4R,6aR)-5-benzyl-2,2-dimethyltetrahydro-4H-[1,3] dioxolo[4,5-c]pyrrol-4-yl)ethane-1,2-diol

1,4-dideoxy-1,4-imino-D-mannitol hydrochloride