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

Base Information

Chemical Name:(2S,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-cyano-3-hydroxymethylpyrrolidine
CAS No.:159516-91-3
Molecular Formula:C₁₉H₂₆N₂O₄
Molecular Weight:346.426
Hs Code.:

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

Chemical Property:

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

There total 20 articles about (2S,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-cyano-3-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: 93.0%

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

: 159516-91-3
(2S,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-cyano-3-hydroxymethylpyrrolidine

Guidance literature:: With toluene-4-sulfonic acid; In methanol; chloroform; for 3h; Ambient temperature;
DOI:10.1016/S0040-4020(01)80643-8

Reference yield:

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

: 159516-91-3
(2S,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-cyano-3-hydroxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 9 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

9: 93 percent / p-toluenesulfonic acid monohydrate / CHCl₃; methanol / 3 h / Ambient temperature

With hydrogenchloride; dmap; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform; 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

: 159516-91-3
(2S,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-cyano-3-hydroxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 11 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

11: 93 percent / p-toluenesulfonic acid monohydrate / CHCl₃; methanol / 3 h / Ambient temperature

With hydrogenchloride; dmap; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; chloroform; water; acetic acid; triethylamine; N,N-dimethyl-formamide; acetonitrile; paraffin;
DOI:10.1016/S0040-4020(01)80643-8