(1S,5aR,5bS)-1,2b-Dimethyl-4-((S)-1-phenyl-ethyl)-hexahydro-4-aza-cyclopropa[cd]indene-2,3-dione

Base Information

• Chemical Name: (1S,5aR,5bS)-1,2b-Dimethyl-4-((S)-1-phenyl-ethyl)-hexahydro-4-aza-cyclopropa[cd]indene-2,3-dione
• CAS No.: 139025-19-7
• Molecular Formula: C₁₈H₂₁NO₂
• Molecular Weight: 283.37
• Mol file: 139025-19-7.mol

Synonyms:(1S,5aR,5bS)-1,2b-Dimethyl-4-((S)-1-phenyl-ethyl)-hexahydro-4-aza-cyclopropa[cd]indene-2,3-dione

Chemical Property of (1S,5aR,5bS)-1,2b-Dimethyl-4-((S)-1-phenyl-ethyl)-hexahydro-4-aza-cyclopropa[cd]indene-2,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5aR,5bS)-1,2b-Dimethyl-4-((S)-1-phenyl-ethyl)-hexahydro-4-aza-cyclopropa[cd]indene-2,3-dione

There total 12 articles about (1S,5aR,5bS)-1,2b-Dimethyl-4-((S)-1-phenyl-ethyl)-hexahydro-4-aza-cyclopropa[cd]indene-2,3-dione 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: 90.0%

(-)-(1S,2S,6S,9R,1'S)-2-methyl-4-(1'-phenylethyl)-4-azatricyclo<4.3.0.02.9>nonan-3,8-dione (139025-18-6) + methyl iodide (74-88-4) → (-)-(1S,2S,6R,7S,9R,1'S)-2,7-dimethyl-4-(1'-phenylethyl)-4-azatricyclo<4.3.0.02.9>nonan-3,8-dione (139025-19-7)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; at -80 - -30 ℃; for 2h;

DOI:10.1002/hlca.19930760416

Reference yield: 80.0%

(5aS,5bS)-2b-Methyl-4-((S)-1-phenyl-ethyl)-hexahydro-4-aza-cyclopropa[cd]indene-2,3-dione (139025-18-6) + methyl iodide (74-88-4) → (1S,5aR,5bS)-1,2b-Dimethyl-4-((S)-1-phenyl-ethyl)-hexahydro-4-aza-cyclopropa[cd]indene-2,3-dione (139025-19-7)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/0040-4039(91)80484-N

Reference yield:

(1R,4R) 2-<(1'(S)-phenyl)-ethyl>-2-aza-bicyclo<2.2.1>hept-5-ene (95119-33-8) → (1S,5aR,5bS)-1,2b-Dimethyl-4-((S)-1-phenyl-ethyl)-hexahydro-4-aza-cyclopropa[cd]indene-2,3-dione (139025-19-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 61 percent / CH₂Cl₂ / 16 h / -2 °C

2: 81 percent / Zn, NH₄Cl / methanol

3: 82 percent / LDA / tetrahydrofuran

4: MCPBA, NaHCO₃ / CH₂Cl₂

5: 80 percent / LiNEt₂ / diethyl ether

6: 95 percent / DMSO, (COCl)2, NEt₃

7: 80 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide

With oxalyl dichloride; lithium diethylamide; sodium hydrogencarbonate; ammonium chloride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;

DOI:10.1016/0040-4039(91)80484-N

upstream raw materials:

(5aS,5bS)-2b-Methyl-4-((S)-1-phenyl-ethyl)-hexahydro-4-aza-cyclopropa[cd]indene-2,3-dione

methyl iodide

(-)-(1S,2S,6S,9R,1'S)-2-methyl-4-(1'-phenylethyl)-4-azatricyclo<4.3.0.0^2.9>nonan-3,8-dione

(1S,6R,1'S)-5-methyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>non-7-en-4-one

Downstream raw materials:

(-)-(1R,5S,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>nonan-4,8-dione

(-)-(1R,5R,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)-3-azabicyclo<4.3.0>nonan-4,8-dione

(-)-δ-N-Normethylskytanthine

(+)-(1R,5R,6R,9S,1'S)-5,9-dimethyl-3-(1'-phenylethyl)spiro<<3>azabicyclo<4.3.0>nonane-8,2''-<1,3>dithiane>