(2R,4S)-1-Allyloxycarbonyl-4-benzoylthio-2-(1-methyl-imidazol-5-ylmethyl)-pyrrolidine

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Chemical Name:(2R,4S)-1-Allyloxycarbonyl-4-benzoylthio-2-(1-methyl-imidazol-5-ylmethyl)-pyrrolidine
CAS No.:156442-06-7
Molecular Formula:C₂₀H₂₃N₃O₃S
Molecular Weight:385.487
Hs Code.:

Synonyms:(2R,4S)-1-Allyloxycarbonyl-4-benzoylthio-2-(1-methyl-imidazol-5-ylmethyl)-pyrrolidine

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Chemical Property of (2R,4S)-1-Allyloxycarbonyl-4-benzoylthio-2-(1-methyl-imidazol-5-ylmethyl)-pyrrolidine

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Technology Process of (2R,4S)-1-Allyloxycarbonyl-4-benzoylthio-2-(1-methyl-imidazol-5-ylmethyl)-pyrrolidine

There total 12 articles about (2R,4S)-1-Allyloxycarbonyl-4-benzoylthio-2-(1-methyl-imidazol-5-ylmethyl)-pyrrolidine 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: 98.0%

: 156442-05-6
(2R,4R)-1-Allyloxycarbonyl-4-hydroxy-2-(1-methyl-imidazol-5-ylmethyl)-pyrrolidine

: 98-91-9
thiobenzoic acid

: 156442-06-7
(2R,4S)-1-Allyloxycarbonyl-4-benzoylthio-2-(1-methyl-imidazol-5-ylmethyl)-pyrrolidine

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1016/S0968-0896(00)00314-X

Reference yield:

: 156440-98-1
(2S,4R)-N-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidine-2-carbaldehyde

: 156442-06-7
(2R,4S)-1-Allyloxycarbonyl-4-benzoylthio-2-(1-methyl-imidazol-5-ylmethyl)-pyrrolidine

Guidance literature:: Multi-step reaction with 9 steps

1: 56 percent / LDA / 1,2-dimethoxy-ethane; tetrahydrofuran; hexane / 2.5 h / -68 - -5 °C

2: 76.4 percent / Raney-Ni / ethanol / 2.5 h / 20 °C

3: SOCl₂ / 1 h / -20 °C

4: 211.7 g / Et₃N / CH₂Cl₂ / 1 h / -15 - -5 °C

5: 130.7 g / AIBN; n-Bu₃SnH / toluene / 1.75 h / Heating

6: HCO₂NH₄ / Pd/C / methanol / 0.67 h / Heating

7: 66.2 g / aq. NaOH / tetrahydrofuran / 0.17 h / 0 - 5 °C / pH 8.5 - 10

8: aq. HCl / methanol / 1.75 h / 0 - 20 °C

9: 98 percent / PPh₃; DEAD / tetrahydrofuran / 2 h / 20 °C

With hydrogenchloride; sodium hydroxide; thionyl chloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; ammonium formate; nickel; triethylamine; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; toluene; 9: Mitsunobu reaction;
DOI:10.1016/S0968-0896(00)00314-X

Reference yield:

: 156442-03-4
(2R,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-[(1-methylimidazol-5-yl)methyl]pyrrolidine

: 156442-06-7
(2R,4S)-1-Allyloxycarbonyl-4-benzoylthio-2-(1-methyl-imidazol-5-ylmethyl)-pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: HCO₂NH₄ / Pd/C / methanol / 0.67 h / Heating

2: 66.2 g / aq. NaOH / tetrahydrofuran / 0.17 h / 0 - 5 °C / pH 8.5 - 10

3: aq. HCl / methanol / 1.75 h / 0 - 20 °C

4: 98 percent / PPh₃; DEAD / tetrahydrofuran / 2 h / 20 °C

With hydrogenchloride; sodium hydroxide; ammonium formate; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; 4: Mitsunobu reaction;
DOI:10.1016/S0968-0896(00)00314-X