(2S,5R)-4-benzoyloxy-1-tert-butoxycarbonyl-2-cyano-5-hydroxymethylpyrrolidine

Base Information

Chemical Name:(2S,5R)-4-benzoyloxy-1-tert-butoxycarbonyl-2-cyano-5-hydroxymethylpyrrolidine
CAS No.:189458-47-7
Molecular Formula:C₁₈H₂₂N₂O₅
Molecular Weight:346.383
Hs Code.:

Synonyms:(2S,5R)-4-benzoyloxy-1-tert-butoxycarbonyl-2-cyano-5-hydroxymethylpyrrolidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,5R)-4-benzoyloxy-1-tert-butoxycarbonyl-2-cyano-5-hydroxymethylpyrrolidine

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Technology Process of (2S,5R)-4-benzoyloxy-1-tert-butoxycarbonyl-2-cyano-5-hydroxymethylpyrrolidine

There total 7 articles about (2S,5R)-4-benzoyloxy-1-tert-butoxycarbonyl-2-cyano-5-hydroxymethylpyrrolidine 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: 50.0%

: 7677-24-9
trimethylsilyl cyanide

: (2R,3S)-3-Benzoyloxy-2-hydroxymethyl-5-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

: 189458-47-7
(2S,5R)-4-benzoyloxy-1-tert-butoxycarbonyl-2-cyano-5-hydroxymethylpyrrolidine

Guidance literature:: With tin(IV) chloride; In dichloromethane; at -40 ℃; for 45h;
DOI:10.1080/00397919708006067

Reference yield:

: 156045-79-3
bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one

: 189458-47-7
(2S,5R)-4-benzoyloxy-1-tert-butoxycarbonyl-2-cyano-5-hydroxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / Et₃N / CH₂Cl₂ / Ambient temperature

2: 91 percent / CF₃CO₂H / tetrahydrofuran; H₂O / 6 h / Ambient temperature

3: 89 percent / trichloroacetic acid / CHCl₃ / 6 h / Ambient temperature

4: 100 percent / DMAP / CH₂Cl₂ / 12 h / Ambient temperature

5: 95 percent / DIBAL-H / hexane; tetrahydrofuran / 0.33 h / -78 °C

6: 100 percent / p-toluenesulfonic acid / 1.25 h / Ambient temperature

7: 50 percent / SnCl₄ / CH₂Cl₂ / 45 h / -40 °C

With dmap; tin(IV) chloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; trichloroacetic acid; In tetrahydrofuran; hexane; dichloromethane; chloroform; water;
DOI:10.1080/00397919708006067

Reference yield:

: 189458-42-2
(4S,5R)-4-benzoyloxy-5-hydroxymethylpyrrolidin-2-one

: 189458-47-7
(2S,5R)-4-benzoyloxy-1-tert-butoxycarbonyl-2-cyano-5-hydroxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / trichloroacetic acid / CHCl₃ / 6 h / Ambient temperature

2: 100 percent / DMAP / CH₂Cl₂ / 12 h / Ambient temperature

3: 95 percent / DIBAL-H / hexane; tetrahydrofuran / 0.33 h / -78 °C

4: 100 percent / p-toluenesulfonic acid / 1.25 h / Ambient temperature

5: 50 percent / SnCl₄ / CH₂Cl₂ / 45 h / -40 °C

With dmap; tin(IV) chloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; trichloroacetic acid; In tetrahydrofuran; hexane; dichloromethane; chloroform;
DOI:10.1080/00397919708006067