methyl (1S,4S,5R,6S)-4,5-(isopropylidenedioxy)-7-azabicyclo[4.1.0]hept-2-ene-7-carboxylate

Base Information

Chemical Name:methyl (1S,4S,5R,6S)-4,5-(isopropylidenedioxy)-7-azabicyclo[4.1.0]hept-2-ene-7-carboxylate
CAS No.:228245-39-4
Molecular Formula:C₁₁H₁₅NO₄
Molecular Weight:225.244
Hs Code.:

Synonyms:methyl (1S,4S,5R,6S)-4,5-(isopropylidenedioxy)-7-azabicyclo[4.1.0]hept-2-ene-7-carboxylate

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Chemical Property of methyl (1S,4S,5R,6S)-4,5-(isopropylidenedioxy)-7-azabicyclo[4.1.0]hept-2-ene-7-carboxylate

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Technology Process of methyl (1S,4S,5R,6S)-4,5-(isopropylidenedioxy)-7-azabicyclo[4.1.0]hept-2-ene-7-carboxylate

There total 3 articles about methyl (1S,4S,5R,6S)-4,5-(isopropylidenedioxy)-7-azabicyclo[4.1.0]hept-2-ene-7-carboxylate 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:

: 589-87-7
1,4-bromoiodobenzene

: 228245-39-4
methyl (1S,4S,5R,6S)-4,5-(isopropylidenedioxy)-7-azabicyclo[4.1.0]hept-2-ene-7-carboxylate

: 219985-31-6
tris[4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)phenyl]phosphane

: tris[4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)phenyl]phosphine oxide

Guidance literature:: Multi-step reaction with 2 steps

1.1: zinc; 1,2-dibromoethane; chlorotrimethylsilane / tetrahydrofuran / 12 h / 25 °C

1.2: 56 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 24 h / 45 °C

2.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C

2.2: 81 percent / diethyl ether; pentane / -78 - 20 °C

With chloro-trimethyl-silane; tert.-butyl lithium; ethylene dibromide; zinc; In tetrahydrofuran; diethyl ether; pentane;
DOI:10.1021/jo000464f

Reference yield:

: 589-87-7
1,4-bromoiodobenzene

: 228245-39-4
methyl (1S,4S,5R,6S)-4,5-(isopropylidenedioxy)-7-azabicyclo[4.1.0]hept-2-ene-7-carboxylate

: 219985-31-6
tris[4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)phenyl]phosphane

: tris[4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)phenyl]phosphine oxide

: 415718-71-7
2,6-dicyanocarbazole

: 460731-70-8
methyl N-[(1S,4S,5S,6R)-2-(1,3-benzodioxol-5-yl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]carbamate

Guidance literature:: Multi-step reaction with 2 steps

1.1: zinc; 1,2-dibromoethane; chlorotrimethylsilane / tetrahydrofuran / 12 h / 25 °C

1.2: 56 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 24 h / 45 °C

2.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C

2.2: 81 percent / diethyl ether; pentane / -78 - 20 °C

With chloro-trimethyl-silane; tert.-butyl lithium; ethylene dibromide; zinc; In tetrahydrofuran; diethyl ether; pentane;
DOI:10.1021/jo000464f

Reference yield:

: 589-87-7
1,4-bromoiodobenzene

: 228245-39-4
methyl (1S,4S,5R,6S)-4,5-(isopropylidenedioxy)-7-azabicyclo[4.1.0]hept-2-ene-7-carboxylate

: 219985-31-6
tris[4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)phenyl]phosphane

: tris[4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)phenyl]phosphine oxide

: 415718-71-7
2,6-dicyanocarbazole

: 460731-70-8
methyl N-[(1S,4S,5S,6R)-2-(1,3-benzodioxol-5-yl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]carbamate

: 2,6-diamidinocarbazole dihydrochloride

Guidance literature:: Multi-step reaction with 6 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran / 4 h / -40 °C

1.2: 2.25 h / -40 - 20 °C

1.3: 2 h / 20 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 80 °C

3.1: triethylsilane; bis-triphenylphosphine-palladium(II) chloride; acetic anhydride; N-ethyl-N,N-diisopropylamine; lithium chloride / N,N-dimethyl-formamide / 90 °C / Inert atmosphere

4.1: sodium tris(acetoxy)borohydride; acetic acid / benzene / 1 h / Reflux; Inert atmosphere

5.1: 1H-tetrazole / dichloromethane

5.2: 0 - 20 °C

6.1: hydrogenchloride / ethyl acetate / 2 h / 20 °C / Saturated solution

With 1H-tetrazole; hydrogenchloride; triethylsilane; bis-triphenylphosphine-palladium(II) chloride; isopropylmagnesium chloride; acetic anhydride; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1002/jlcr.1755