(2S,3S,5S)-2-Benzyl-3-hydroxy-5-((E)-non-1-enyl)-pyrrolidine-1-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3S,5S)-2-Benzyl-3-hydroxy-5-((E)-non-1-enyl)-pyrrolidine-1-carboxylic acid methyl ester
CAS No.:337963-40-3
Molecular Formula:C₂₂H₃₃NO₃
Molecular Weight:359.509
Hs Code.:

Synonyms:(2S,3S,5S)-2-Benzyl-3-hydroxy-5-((E)-non-1-enyl)-pyrrolidine-1-carboxylic acid methyl ester

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Chemical Property of (2S,3S,5S)-2-Benzyl-3-hydroxy-5-((E)-non-1-enyl)-pyrrolidine-1-carboxylic acid methyl ester

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Technology Process of (2S,3S,5S)-2-Benzyl-3-hydroxy-5-((E)-non-1-enyl)-pyrrolidine-1-carboxylic acid methyl ester

There total 9 articles about (2S,3S,5S)-2-Benzyl-3-hydroxy-5-((E)-non-1-enyl)-pyrrolidine-1-carboxylic acid methyl ester 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: 80.0%

: 131013-27-9
(2S,3S,5S)-5-formyl-2-(phenylmethyl)-1-carbomethoxy-3-pyrrolidinol

: 71344-40-6
n-octyltriphenylphosphonium iodide

: 337963-40-3
(2S,3S,5S)-2-Benzyl-3-hydroxy-5-((E)-non-1-enyl)-pyrrolidine-1-carboxylic acid methyl ester

Guidance literature:: With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃;
DOI:10.3987/com-00-s(i)69

Reference yield:

: 6372-14-1
N-((benzyloxy)carbonyl)-L-phenylalaninol

: 337963-40-3
(2S,3S,5S)-2-Benzyl-3-hydroxy-5-((E)-non-1-enyl)-pyrrolidine-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: NaHCO₃; NaOCl; NaBr / TEMPO / ethyl acetate; toluene; H₂O / -5 °C

2: 77 percent / SnCl₄ / CH₂Cl₂ / -78 °C

3: 87 percent / t-C₄H₉OOH / VO(acac)2 / CH₂Cl₂ / 20 °C

4: 100 percent / H₂ / Pd/C / methanol / 20 °C

5: NaHCO₃ / CH₂Cl₂; H₂O / 20 °C

6: 72 percent / NaHCO₃; NaOCl; NaBr / TEMPO / H₂O; toluene; ethyl acetate / -5 °C

7: 80 percent / n-C₄H₉Li / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

With tert.-butylhydroperoxide; sodium hypochlorite; n-butyllithium; hydrogen; tin(IV) chloride; sodium hydrogencarbonate; sodium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium on activated charcoal; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; ethyl acetate; toluene;
DOI:10.3987/com-00-s(i)69

Reference yield:

: 59830-60-3
benzyl (1S)-(1-formyl-2-phenylethyl)carbamate

: 337963-40-3
(2S,3S,5S)-2-Benzyl-3-hydroxy-5-((E)-non-1-enyl)-pyrrolidine-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 77 percent / SnCl₄ / CH₂Cl₂ / -78 °C

2: 87 percent / t-C₄H₉OOH / VO(acac)2 / CH₂Cl₂ / 20 °C

3: 100 percent / H₂ / Pd/C / methanol / 20 °C

4: NaHCO₃ / CH₂Cl₂; H₂O / 20 °C

5: 72 percent / NaHCO₃; NaOCl; NaBr / TEMPO / H₂O; toluene; ethyl acetate / -5 °C

6: 80 percent / n-C₄H₉Li / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

With tert.-butylhydroperoxide; sodium hypochlorite; n-butyllithium; hydrogen; tin(IV) chloride; sodium hydrogencarbonate; sodium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium on activated charcoal; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; ethyl acetate; toluene;
DOI:10.3987/com-00-s(i)69