(2S,3R,5S)-5-benzyloxymethyl-2-cyano-1-tert-butoxycarbonyl-3-methoxymethylpyrrolidine

Base Information

Chemical Name:(2S,3R,5S)-5-benzyloxymethyl-2-cyano-1-tert-butoxycarbonyl-3-methoxymethylpyrrolidine
CAS No.:152500-37-3
Molecular Formula:C₂₁H₃₀N₂O₅
Molecular Weight:390.48
Hs Code.:

Synonyms:(2S,3R,5S)-5-benzyloxymethyl-2-cyano-1-tert-butoxycarbonyl-3-methoxymethylpyrrolidine

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Chemical Property of (2S,3R,5S)-5-benzyloxymethyl-2-cyano-1-tert-butoxycarbonyl-3-methoxymethylpyrrolidine

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Technology Process of (2S,3R,5S)-5-benzyloxymethyl-2-cyano-1-tert-butoxycarbonyl-3-methoxymethylpyrrolidine

There total 18 articles about (2S,3R,5S)-5-benzyloxymethyl-2-cyano-1-tert-butoxycarbonyl-3-methoxymethylpyrrolidine 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: 26.0%

: 7677-24-9
trimethylsilyl cyanide

: (3S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-methoxy-3-methoxymethylpyrrolidine

: 152500-37-3
(2S,3R,5S)-5-benzyloxymethyl-2-cyano-1-tert-butoxycarbonyl-3-methoxymethylpyrrolidine

: 152500-38-4
(2R,3R,5S)-5-benzyloxymethyl-2-cyano-1-tert-butoxycarbonyl-3-methoxymethylpyrrolidine

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

: 152500-37-3
(2S,3R,5S)-5-benzyloxymethyl-2-cyano-1-tert-butoxycarbonyl-3-methoxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 8 steps

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

2: 99 percent / 3 h / 75 °C

3: 89 percent / 1M hydrochloric acid / tetrahydrofuran; H₂O / 1 h / Ambient temperature

4: 81 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol; acetic acid / 2 h / -10 °C

5: 82 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 12 h / Ambient temperature

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

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

8: 69 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

With hydrogenchloride; dmap; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium cyanoborohydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; acetic acid; triethylamine; acetonitrile;
DOI:10.1016/S0040-4020(01)80643-8

Reference yield:

: 152500-26-0
(S)-5-(hydroxymethyl)-1-(4-methoxyphenylmethyl)-2-pyrrolidinone

: 152500-37-3
(2S,3R,5S)-5-benzyloxymethyl-2-cyano-1-tert-butoxycarbonyl-3-methoxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 10 steps

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

2: 83 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 2 h / Ambient temperature

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

4: 99 percent / 3 h / 75 °C

5: 89 percent / 1M hydrochloric acid / tetrahydrofuran; H₂O / 1 h / Ambient temperature

6: 81 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol; acetic acid / 2 h / -10 °C

7: 82 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 12 h / Ambient temperature

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

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

10: 69 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

With hydrogenchloride; dmap; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; acetic acid; triethylamine; N,N-dimethyl-formamide; acetonitrile; paraffin;
DOI:10.1016/S0040-4020(01)80643-8