(2R,5S)-2-Benzyloxymethyl-5-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2R,5S)-2-Benzyloxymethyl-5-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:159516-83-3
Molecular Formula:C₁₈H₂₄N₂O₃
Molecular Weight:316.4
Hs Code.:

Synonyms:(2R,5S)-2-Benzyloxymethyl-5-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2R,5S)-2-Benzyloxymethyl-5-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2R,5S)-2-Benzyloxymethyl-5-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 15 articles about (2R,5S)-2-Benzyloxymethyl-5-cyano-pyrrolidine-1-carboxylic acid tert-butyl 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: 27.0%

: 7677-24-9
trimethylsilyl cyanide

: (R)-2-Benzyloxymethyl-5-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

: 152612-41-4
(2S,5S)-2-Benzyloxymethyl-5-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester

: 159516-83-3
(2R,5S)-2-Benzyloxymethyl-5-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1016/S0040-4020(01)80643-8

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 159516-83-3
(2R,5S)-2-Benzyloxymethyl-5-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / 4-dimethylaminopyridine / acetonitrile; triethylamine / 3 h / Ambient temperature

2: diisobutylaluminium hydride / hexane; tetrahydrofuran / -78 deg C, 1 h, then 0 deg C, 2 h

3: pyridinium p-toluenesulfonate / 12 h / Ambient temperature

4: NaH / paraffin; dimethylformamide / 1 h / Ambient temperature

5: 27 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

With dmap; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; triethylamine; N,N-dimethyl-formamide; acetonitrile; paraffin;
DOI:10.1016/S0040-4020(01)80643-8

Reference yield:

: 6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6
D-Glutamic acid

: 159516-83-3
(2R,5S)-2-Benzyloxymethyl-5-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 39 percent / 2M sodium hydroxide, sodium borohydride / H₂O / 3.5 h / Ambient temperature

2: 83 percent / thionyl chloride / 3 h / Heating

3: 92 percent / lithium chloride, sodium borohydride / ethanol; tetrahydrofuran / 2 h / Ambient temperature

4: 96 percent / NaH / dimethylformamide; paraffin / 1 h / Ambient temperature

5: 86 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 2 h / Ambient temperature

6: 96 percent / 4-dimethylaminopyridine / acetonitrile; triethylamine / 3 h / Ambient temperature

7: diisobutylaluminium hydride / hexane; tetrahydrofuran / 1 h / -78 °C

8: pyridinium p-toluenesulfonate / 3 h / Ambient temperature

9: 27 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

With dmap; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; lithium chloride; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; triethylamine; N,N-dimethyl-formamide; acetonitrile; paraffin;
DOI:10.1016/S0040-4020(01)80643-8