(2S,4S)-1-tert-butyl 2-methyl 4-cyanopyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (2S,4S)-1-tert-butyl 2-methyl 4-cyanopyrrolidine-1,2-dicarboxylate
• CAS No.: 487048-28-2
• Molecular Formula: C12H18 N2 O4
• Molecular Weight: 254.286
• Hs Code.: 2933990090
• European Community (EC) Number: 688-361-6
• DSSTox Substance ID: DTXSID40590516
• Wikidata: Q72459188
• Mol file: 487048-28-2.mol

Synonyms:487048-28-2;(2S,4S)-1-tert-butyl 2-methyl 4-cyanopyrrolidine-1,2-dicarboxylate;Boc-cis-4-cyano-L-proline methyl ester;N-Boc-cis-4-cyano-L-proline methyl ester;1-tert-butyl 2-methyl (2S,4S)-4-cyanopyrrolidine-1,2-dicarboxylate;1-O-tert-butyl 2-O-methyl (2S,4S)-4-cyanopyrrolidine-1,2-dicarboxylate;1,2-Pyrrolidinedicarboxylic acid, 4-cyano-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,4S)-;N-BOC-CIS-4-CYANO-L-PROLINEMETHYLESTER;SCHEMBL203240;DTXSID40590516;MFCD03787928;SC5051;AKOS015850933;AKOS015907655;AM86115;AC-28746;AS-72013;cis-N-Boc-4-cyano-L-proline methyl ester;CS-0186054;A26546;(2S,4S)-1-(tert-butoxycarbonyl)-4-cyano-2-methylpyrrolidine-2-carboxylic acid;1,2-pyrrolidinedicarboxylic acid,4-cyano-,1-tert-butyl 2-methyl ester,(2s,4s)-;1,2-Pyrrolidinedicarboxylicacid,4-cyano-,1-(1,1-dimethylethyl)2-methyl ester,(2S,4S)-

Chemical Property of (2S,4S)-1-tert-butyl 2-methyl 4-cyanopyrrolidine-1,2-dicarboxylate

Chemical Property:

• Boiling Point: 366.4±42.0 °C(Predicted)
• PKA: -5.81±0.60(Predicted)
• PSA: 79.63000
• Density: 1.17
• LogP: 1.24648
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 254.12665706
• Heavy Atom Count: 18
• Complexity: 391

Purity/Quality:

99%, ^*data from raw suppliers

N-Boc-cis-4-cyano-L-prolinemethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)OC)C#N
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@H]1C(=O)OC)C#N

Technology Process of (2S,4S)-1-tert-butyl 2-methyl 4-cyanopyrrolidine-1,2-dicarboxylate

There total 2 articles about (2S,4S)-1-tert-butyl 2-methyl 4-cyanopyrrolidine-1,2-dicarboxylate 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:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (487048-28-2)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 20 °C

2: triethylamine / dichloromethane / 1.83 h / 0 - 20 °C

3: dimethyl sulfoxide / 72 h / 55 °C / Inert atmosphere

With triethylamine; In dichloromethane; dimethyl sulfoxide;

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → 1-(tert-butyl) 2-methyl (2S,4R)-4-cyanopyrrolidine-1 ,2-dicarboxylate (194163-91-2) + (2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (487048-28-2)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / acetonitrile / 0 - 20 °C

2: triethylamine / dichloromethane / 20 h / 0 - 20 °C

3: dimethyl sulfoxide / 4 h / 80 °C

With triethylamine; In dichloromethane; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/anie.201302014

Reference yield:

(2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (487048-28-2) → methyl {(2S)-1-[(2S,5S)-2-(9-{2-[(2S,4S)-1-{(2R)-2-[(methoxycarbonyl)amino]-2-phenylacetyl}-4-(methoxymethyl)pyrrolidin-2-yl]-1H-imidazol-5-yl}-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate (1377049-84-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: hydrogenchloride / 1,4-dioxane / 16 h / 20 °C

1.2: 12 h / 20 °C

2.1: water; sodium hydroxide / tert-Amyl alcohol / 5.25 h / 0 °C / Cooling with ice

3.1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice

4.1: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice

5.1: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice

6.1: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C

7.1: caesium carbonate / 4 h / 20 °C

8.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C

9.1: caesium carbonate / 20 h / 50 °C

10.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C

11.1: manganese(IV) oxide / dichloromethane / 13 h

12.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C

13.1: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C

With hydrogenchloride; manganese(IV) oxide; sodium tetrahydroborate; 2,6-di-tert-butyl-pyridine; pyridinium hydrobromide perbromide; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; ammonium acetate; water; silver trifluoromethanesulfonate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; tert-Amyl alcohol; dichloromethane; 2-methoxy-ethanol; N,N-dimethyl-formamide; toluene;

upstream raw materials:

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

(2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

(2S,4S)-2-[5-(4-bromo-phenyl)-1H-imidazol-2-yl]-4-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4S)-4-cyano-2-{5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4S)-4-Cyano-2-(5-{4'-[2-((2S,5S)-5-methoxycarbonylamino-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indol-2-yl)-3H-imidazol-4-yl]-biphenyl-4-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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