(2R,3R,5R)-3-benzoyloxy-2-cyano-1-methoxycarbonyl-5-methylpyrrolidine

Base Information

• Chemical Name: (2R,3R,5R)-3-benzoyloxy-2-cyano-1-methoxycarbonyl-5-methylpyrrolidine
• CAS No.: 213699-39-9
• Molecular Formula: C₁₅H₁₆N₂O₄
• Molecular Weight: 288.303
• Mol file: 213699-39-9.mol

Synonyms:(2R,3R,5R)-3-benzoyloxy-2-cyano-1-methoxycarbonyl-5-methylpyrrolidine

Chemical Property of (2R,3R,5R)-3-benzoyloxy-2-cyano-1-methoxycarbonyl-5-methylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,5R)-3-benzoyloxy-2-cyano-1-methoxycarbonyl-5-methylpyrrolidine

There total 7 articles about (2R,3R,5R)-3-benzoyloxy-2-cyano-1-methoxycarbonyl-5-methylpyrrolidine 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: 59.0%

trimethylsilyl cyanide (7677-24-9) + (3R,5R)-3-benzoyloxy-2-methoxy-1-methoxycarbonyl-5-methylpyrrolidine → (2S,3R,5R)-3-benzoyloxy-2-cyano-1-methoxycarbonyl-5-methylpyrrolidine (213699-40-2) + (2R,3R,5R)-3-benzoyloxy-2-cyano-1-methoxycarbonyl-5-methylpyrrolidine (213699-39-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4020(98)00604-8

Reference yield:

benzoyl chloride (98-88-4) → (2R,3R,5R)-3-benzoyloxy-2-cyano-1-methoxycarbonyl-5-methylpyrrolidine (213699-39-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / pyridine / 20 h / Ambient temperature

2: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

3: 1.) LiN(TMS)2 / 1) THF, -15 deg C, 30 min; 2) THF, -15 deg C, 1 h

4: LiEt₃BH / tetrahydrofuran / -78 °C

5: pyridinium p-toluenesulfonate / Ambient temperature

6: 59 percent / BF₃*Et₂O / CH₂Cl₂ / -78 °C

With pyridine; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; lithium triethylborohydride; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(98)00604-8

Reference yield:

tert-butyl (2R,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-methylpyrrolidine-1-carboxylate (132945-96-1) → (2R,3R,5R)-3-benzoyloxy-2-cyano-1-methoxycarbonyl-5-methylpyrrolidine (213699-39-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / RuO₂*xH₂O, aq. NaIO₄ / ethyl acetate / 3 h / Ambient temperature

2: 92 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

3: 82 percent / pyridine / 20 h / Ambient temperature

4: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

5: 1.) LiN(TMS)2 / 1) THF, -15 deg C, 30 min; 2) THF, -15 deg C, 1 h

6: LiEt₃BH / tetrahydrofuran / -78 °C

7: pyridinium p-toluenesulfonate / Ambient temperature

8: 59 percent / BF₃*Et₂O / CH₂Cl₂ / -78 °C

With pyridine; ruthenium(IV) oxide; sodium periodate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; lithium triethylborohydride; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4020(98)00604-8

upstream raw materials:

trimethylsilyl cyanide

benzoyl chloride

(3R,5R)-3-benzoyloxy-5-methyl-2-pyrrolidinone

tert-butyl (2R,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-methylpyrrolidine-1-carboxylate

Downstream raw materials:

(2R,3R,5R)-3-hydroxy-5-methylproline

Refernces