(3S,5S,7R,7aS)-1-benzyl-5-tert-butoxycarbonyl-7-cyano-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole

Base Information

• Chemical Name: (3S,5S,7R,7aS)-1-benzyl-5-tert-butoxycarbonyl-7-cyano-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole
• CAS No.: 175792-76-4
• Molecular Formula: C₂₆H₃₁N₃O₂
• Molecular Weight: 417.551

Synonyms:(3S,5S,7R,7aS)-1-benzyl-5-tert-butoxycarbonyl-7-cyano-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole

Chemical Property of (3S,5S,7R,7aS)-1-benzyl-5-tert-butoxycarbonyl-7-cyano-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole

Chemical Property:

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Technology Process of (3S,5S,7R,7aS)-1-benzyl-5-tert-butoxycarbonyl-7-cyano-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole

There total 2 articles about (3S,5S,7R,7aS)-1-benzyl-5-tert-butoxycarbonyl-7-cyano-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole 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: 27.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (S)-1-benzyl-4-phenyl-4,5-dihydroimidazole (175792-71-9) + methacrylonitrile (126-98-7,25067-61-2) → (3S,5S,7S,7aR)-1-benzyl-5-t-butoxycarbonyl-7-cyano-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole (175893-13-7) + (3S,5S,7R,7aS)-1-benzyl-5-tert-butoxycarbonyl-7-cyano-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole (175792-76-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 6h; diastereoselective reaction; Reflux; Inert atmosphere;

DOI:10.1039/c0ob00529k

Reference yield: 4.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (S)-1-benzyl-4-phenyl-4,5-dihydroimidazole (175792-71-9) + methacrylonitrile (126-98-7,25067-61-2) → (3S,5S,7R,7aS)-1-benzyl-5-tert-butoxycarbonyl-7-cyano-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole (175792-76-4) + (3S,5S,7S,7aS)-1-Benzyl-7-cyano-7-methyl-3-phenyl-hexahydro-pyrrolo[1,2-a]imidazole-5-carboxylic acid tert-butyl ester

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 6h; Heating;

DOI:10.1016/0040-4039(96)00113-X

Reference yield: 80.0%

(3S,5S,7R,7aS)-1-benzyl-5-tert-butoxycarbonyl-7-cyano-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole (175792-76-4) → (2S,4R)-1-[(S)-2-benzylamino-1-phenylethyl]-2-tert-butoxycarbonyl-4-cyano-4-methylpyrrolidine

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)00114-1

upstream raw materials:

bromoacetic acid tert-butyl ester

(S)-1-benzyl-4-phenyl-4,5-dihydroimidazole

methacrylonitrile

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