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

Base Information

• Chemical Name: (3R,5R,7S,7aR)-1-benzyl-5-tert-butoxycarbonyl-7-methoxycarbonyl-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole
• CAS No.: 175893-21-7
• Molecular Formula: C₂₇H₃₄N₂O₄
• Molecular Weight: 450.578

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

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

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

There total 2 articles about (3R,5R,7S,7aR)-1-benzyl-5-tert-butoxycarbonyl-7-methoxycarbonyl-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: 62.0%

bromoacetic acid tert-butyl ester (5292-43-3) + methacrylic acid methyl ester (80-62-6,114512-63-9,143476-91-9,25188-98-1,9011-14-7) + (R)-1-benzyl-4-phenyl-4,5-dihydroimidazole (175792-72-0) → (3R,5R,7S,7aR)-1-benzyl-5-tert-butoxycarbonyl-7-methoxycarbonyl-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole (175893-21-7)

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:

(R)-N1-benzyl-1-phenylethane-1,2-diamine (155220-77-2) → (3R,5R,7S,7aR)-1-benzyl-5-tert-butoxycarbonyl-7-methoxycarbonyl-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole (175893-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1: TsOH / Heating

2: 62 percent / DBU / tetrahydrofuran / 6 h / Heating

With toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;

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

Reference yield: 76.0%

(3R,5R,7S,7aR)-1-benzyl-5-tert-butoxycarbonyl-7-methoxycarbonyl-7-methyl-3-phenylhexahydropyrrolo[1,2-a]imidazole (175893-21-7) → (2R,4S)-1-[(R)-2-benzylamino-1-phenylethyl]-2-tert-butoxycarbonyl-4-methoxycarbonyl-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

methacrylic acid methyl ester

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

(R)-N¹-benzyl-1-phenylethane-1,2-diamine

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