tert-butyl (2S,5S)-2-(hydroxymethyl)-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

Base Information

Chemical Name:tert-butyl (2S,5S)-2-(hydroxymethyl)-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate
CAS No.:1356115-72-4
Molecular Formula:C₁₆H₂₁NO₃
Molecular Weight:275.348
Hs Code.:

Synonyms:tert-butyl (2S,5S)-2-(hydroxymethyl)-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

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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 tert-butyl (2S,5S)-2-(hydroxymethyl)-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

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Technology Process of tert-butyl (2S,5S)-2-(hydroxymethyl)-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

There total 1 articles about tert-butyl (2S,5S)-2-(hydroxymethyl)-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate 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: 37.0%

: 501096-26-0
(2RS,5S)-1-(tert-butoxycarbonyl)-2-phenyl-5-carbomethoxy-3-pyrroline

: 1356115-73-5
tert-butyl (2S,5R)-2-(hydroxymethyl)-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

: 1356115-72-4
tert-butyl (2S,5S)-2-(hydroxymethyl)-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

Guidance literature:: With sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; ethanol; at 20 ℃; for 3h; stereoselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201100886

Reference yield:

: 1356115-72-4
tert-butyl (2S,5S)-2-(hydroxymethyl)-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

: 1356116-06-7
C₁₆H₂₃NO₅

Guidance literature:: With potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 20 ℃; for 12h; stereoselective reaction;
DOI:10.1002/ejoc.201100886

Reference yield:

: 1356115-72-4
tert-butyl (2S,5S)-2-(hydroxymethyl)-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

: 1356115-75-7
(2R,3R,3aS,7aR)-3-hydroxy-2-phenyl-1,2,3,3a-tetrahydropyrano-[3,2-b]pyrrol-5(7aH)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 12 h / 20 °C

2.1: toluene-4-sulfonic acid / acetone / 1 h / Inert atmosphere

3.1: 4-methylmorpholine N-oxide / dichloromethane / 0.17 h / Inert atmosphere; Molecular sieve

3.2: 0.33 h / 20 °C / Inert atmosphere; Molecular sieve

4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C / Inert atmosphere

4.2: 1 h / Inert atmosphere

5.1: toluene-4-sulfonic acid / methanol / 0.5 h / 60 °C / Microwave irradiation

6.1: toluene-4-sulfonic acid / acetonitrile / 1 h / 60 °C / Microwave irradiation

With potassium osmate(VI) dihydrate; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; mineral oil; tert-butyl alcohol; 4.1: Horner-Wadsworth-Emmons olefination / 4.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1002/ejoc.201100886