tert-butyl (2S,5R)-2-[(tert-butyldimethylsilyloxy)methyl]-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

Base Information

• Chemical Name: tert-butyl (2S,5R)-2-[(tert-butyldimethylsilyloxy)methyl]-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate
• CAS No.: 1356116-09-0
• Molecular Formula: C₂₂H₃₅NO₃Si
• Molecular Weight: 389.61

Synonyms:tert-butyl (2S,5R)-2-[(tert-butyldimethylsilyloxy)methyl]-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

Chemical Property of tert-butyl (2S,5R)-2-[(tert-butyldimethylsilyloxy)methyl]-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

Chemical Property:

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Technology Process of tert-butyl (2S,5R)-2-[(tert-butyldimethylsilyloxy)methyl]-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

There total 2 articles about tert-butyl (2S,5R)-2-[(tert-butyldimethylsilyloxy)methyl]-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate 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: 87.0%

tert-butyl (2S,5R)-2-(hydroxymethyl)-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate (1356115-73-5) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyl (2S,5R)-2-[(tert-butyldimethylsilyloxy)methyl]-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate (1356116-09-0)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1002/ejoc.201100886

Reference yield:

(2RS,5S)-1-(tert-butoxycarbonyl)-2-phenyl-5-carbomethoxy-3-pyrroline (501096-26-0) → tert-butyl (2S,5R)-2-[(tert-butyldimethylsilyloxy)methyl]-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate (1356116-09-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate; calcium chloride / tetrahydrofuran; ethanol / 3 h / 20 °C / Inert atmosphere

2: 1H-imidazole / dichloromethane / 12 h / 20 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1002/ejoc.201100886

Reference yield: 70.0%

tert-butyl (2S,5R)-2-[(tert-butyldimethylsilyloxy)methyl]-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate (1356116-09-0) → tert-butyl (1R,2R,4S,5S)-2-[(tert-butyldimethylsilyloxy)methyl]-4-phenyl-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (1356115-90-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In toluene; at 20 ℃; for 24h;

DOI:10.1002/ejoc.201100886

upstream raw materials:

tert-butyl (2S,5R)-2-(hydroxymethyl)-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

tert-butyldimethylsilyl chloride

(2RS,5S)-1-(tert-butoxycarbonyl)-2-phenyl-5-carbomethoxy-3-pyrroline

Downstream raw materials:

tert-butyl (1R,2R,4S,5S)-2-[(tert-butyldimethylsilyloxy)methyl]-4-phenyl-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

tert-butyl (1R,2R,4S,5S)-2-(hydroxymethyl)-4-phenyl-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

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