(1R,3S,5R)-5-methyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester

Base Information

• Chemical Name: (1R,3S,5R)-5-methyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester
• CAS No.: 1306734-44-0
• Molecular Formula: C₁₂H₁₉NO₄
• Molecular Weight: 241.287

Synonyms:(1R,3S,5R)-5-methyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester

Chemical Property of (1R,3S,5R)-5-methyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester

Chemical Property:

Purity/Quality:

99%, ^*data from raw suppliers

(1R,3S,5R)-5-Methyl-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylicacid2-tert-butylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (1R,3S,5R)-5-Methyl-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester can be used to prepare indole analogs as complement factor D?inhibitors for treating age-related macular degeneration. It can also be utilized to synthesize hepatitis C virus inhibitors.

Technology Process of (1R,3S,5R)-5-methyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester

There total 21 articles about (1R,3S,5R)-5-methyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 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: 57.56%

(1R,3S,5R)-3-hydroxymethyl-5-methyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester → (1R,3S,5R)-5-methyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester (1306734-44-0)

Guidance literature:

With sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In water; acetonitrile; at 35 ℃; for 8h; Large scale;

Reference yield: 52.4%

(1R,3S,5R)-2-tert-butyl 3-methyl 5-methyl-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylate (1250939-98-0) → (1R,3S,5R)-5-methyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester (1306734-44-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 3h;

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → (1R,3S,5R)-5-methyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester (1306734-44-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dmap; triethylamine / dichloromethane / 3 h / 5 - 20 °C

2.1: dmap / dichloromethane / 5 - 20 °C

3.1: tert-Butoxybis(dimethylamino)methane

3.2: 50 °C

4.1: lithium triethylborohydride / tetrahydrofuran / -78 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / toluene / 2 h / 70 °C

6.1: diethylzinc / toluene / 0.5 h / -30 °C / Large scale

6.2: 4.5 h / -30 - -2 °C / Large scale

7.1: sodium methylate; methanol / 2 h / 0 - 25 °C / Large scale

8.1: sodium dihydrogenphosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium chlorite; sodium hypochlorite / water; acetonitrile / 8 h / 35 °C / Large scale

With methanol; dmap; sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-Butoxybis(dimethylamino)methane; diethylzinc; sodium methylate; lithium triethylborohydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile;

upstream raw materials:

O₁-tert-butyl O₂-methyl (2S)-4-methyl-5-oxo-pyrrolidine-1,2-dicarboxylate

(S)-1-tert-butyl 2-methyl 4-methyl-2,3-dihydro-1H-pyrrole-1,2-dicarboxylate

(1R,3S,5R)-2-tert-butyl 3-methyl 5-methyl-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylate

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

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