2-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 2-(1,1-dimethylethyl) 3-ethyl ester, (1S,3R,5S)-

Base Information

Chemical Name:2-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 2-(1,1-dimethylethyl) 3-ethyl ester, (1S,3R,5S)-
CAS No.:871727-40-1
Molecular Formula:C13H21NO4
Molecular Weight:255.314
Hs Code.:

Synonyms:

Suppliers and Price of 2-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 2-(1,1-dimethylethyl) 3-ethyl ester, (1S,3R,5S)-

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 2-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 2-(1,1-dimethylethyl) 3-ethyl ester, (1S,3R,5S)-

Chemical Property:

Purity/Quality:: 99%, ^*data from raw suppliers

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Hazard Codes:

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Technology Process of 2-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 2-(1,1-dimethylethyl) 3-ethyl ester, (1S,3R,5S)-

There total 2 articles about 2-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 2-(1,1-dimethylethyl) 3-ethyl ester, (1S,3R,5S)- 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:

: 68766-96-1
ethyl (R)-2-pyrrolidone-5-carboxylate

: 871727-40-1
2-tert-butyl 3-ethyl (1S,3R,5S)-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: dmap

2: lithium triethylborohydride / toluene / -70 - -60 °C

3: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine

4: diethylzinc / toluene; 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C

With dmap; diethylzinc; lithium triethylborohydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In 1,2-dimethoxyethane; dichloromethane; toluene;
DOI:10.1016/j.bmc.2013.12.061

Reference yield:

: 68766-96-1
ethyl (R)-2-pyrrolidone-5-carboxylate

: 871727-37-6
2-tert-butyl 3-ethyl (1R,3R,5R)-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylate

: 871727-40-1
2-tert-butyl 3-ethyl (1S,3R,5S)-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: dmap / toluene / 20 °C

2: lithium triethylborohydride / toluene / 0.5 h / -50 - -45 °C

3: dmap; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride / tetrahydrofuran / 3 h / -45 - 25 °C

4: diethylzinc / toluene / 6 h / 0 °C

With dmap; diethylzinc; lithium triethylborohydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In tetrahydrofuran; toluene;

Reference yield:

: 871727-40-1
2-tert-butyl 3-ethyl (1S,3R,5S)-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylate

: (1aS,4S,6aR,7aS)-5-{(2S)-2-cyclohexyl-2-[(N-methyl-l-alanyl)amino]acetyl}-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]octahydro-1H-cyclopropa[4,5]pyrrolo[1,2-a]pyrazine-4-carboxamide dihydrochloride

Guidance literature:: Multi-step reaction with 14 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C

2: dimethyl sulfoxide; triethylamine; sulfur trioxide pyridine complex / ethyl acetate / 1 h / 0 - 20 °C

3: sodium tris(acetoxy)borohydride / tetrahydrofuran / 18 h / 20 °C

4: hydrogenchloride / ethyl acetate / 3 h / 20 °C

5: triethylamine / toluene / 18 h / 90 °C

6: palladium 10% on activated carbon; hydrogenchloride; hydrogen / methanol / 3 h / 20 °C / 760.05 Torr

7: sodium hydrogencarbonate / tetrahydrofuran / 18 h / 20 °C

8: lithium hydroxide monohydrate / tetrahydrofuran; water / 4 h / 50 °C

9: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 18 h / 20 °C

10: hydrogenchloride / ethyl acetate; methanol / 3 h / 20 °C

11: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C

12: hydrogenchloride / ethyl acetate / 3.5 h / 20 °C

13: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 3 h / 20 °C

14: hydrogenchloride / ethyl acetate / 3 h / 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; sulfur trioxide pyridine complex; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmc.2013.07.020