(2R,3R,5S)-3-acetoxymethyl-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine

Base Information

Chemical Name:(2R,3R,5S)-3-acetoxymethyl-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine
CAS No.:159412-01-8
Molecular Formula:C₂₁H₂₈N₂O₅
Molecular Weight:388.464
Hs Code.:

Synonyms:

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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 (2R,3R,5S)-3-acetoxymethyl-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine

Chemical Property:

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

There total 21 articles about (2R,3R,5S)-3-acetoxymethyl-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine 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: 99.0%

: 108-24-7
acetic anhydride

: 159412-00-7
(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-cyano-3-hydroxymethylpyrrolidine

: 159412-01-8
(2R,3R,5S)-3-acetoxymethyl-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine

Guidance literature:: With pyridine; dmap; for 2h; Ambient temperature;
DOI:10.1016/S0040-4020(01)80643-8

Reference yield:

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

: 159412-01-8
(2R,3R,5S)-3-acetoxymethyl-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine

Guidance literature:: Multi-step reaction with 10 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: 26 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

9: 95 percent / p-toluenesulfonic acid monohydrate / CHCl₃; methanol / 3 h / Ambient temperature

10: 99 percent / pyridine, 4-dimethylaminopyridine / 2 h / Ambient temperature

With pyridine; 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

: 159412-01-8
(2R,3R,5S)-3-acetoxymethyl-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine

Guidance literature:: Multi-step reaction with 12 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: 26 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

11: 95 percent / p-toluenesulfonic acid monohydrate / CHCl₃; methanol / 3 h / Ambient temperature

12: 99 percent / pyridine, 4-dimethylaminopyridine / 2 h / Ambient temperature

With pyridine; 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