(S)-(-)-tert-butyl 4,4-bisbenzyl-2-(hydroxymethyl)pyrrolidinecarboxylate

Base Information

Chemical Name:(S)-(-)-tert-butyl 4,4-bisbenzyl-2-(hydroxymethyl)pyrrolidinecarboxylate
CAS No.:212890-91-0
Molecular Formula:C₂₄H₃₁NO₃
Molecular Weight:381.515
Hs Code.:

Synonyms:(S)-(-)-tert-butyl 4,4-bisbenzyl-2-(hydroxymethyl)pyrrolidinecarboxylate

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Chemical Property of (S)-(-)-tert-butyl 4,4-bisbenzyl-2-(hydroxymethyl)pyrrolidinecarboxylate

Chemical Property:

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Technology Process of (S)-(-)-tert-butyl 4,4-bisbenzyl-2-(hydroxymethyl)pyrrolidinecarboxylate

There total 5 articles about (S)-(-)-tert-butyl 4,4-bisbenzyl-2-(hydroxymethyl)pyrrolidinecarboxylate 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: 84.0%

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

: 212890-90-9
(S)-(+)-(4,4-dibenzylpyrrolidin-2-yl)methan-1-ol

: 212890-91-0
(S)-(-)-tert-butyl 4,4-bisbenzyl-2-(hydroxymethyl)pyrrolidinecarboxylate

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/S0040-4020(98)00485-2

Reference yield:

: 100-39-0
benzyl bromide

: 212890-91-0
(S)-(-)-tert-butyl 4,4-bisbenzyl-2-(hydroxymethyl)pyrrolidinecarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 73 percent / LDA; HMPA / tetrahydrofuran / 5.5 h / -78 °C

2: 97 percent / p-TsOH / methanol / 1 h / Heating

3: 95 percent / LiAlH₄ / tetrahydrofuran / 96 h / 0 - 20 °C

4: 84 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; 1: Alkylation / 2: Ring cleavage / 3: Reduction / 4: Carboxylation;
DOI:10.1016/S0040-4020(98)00485-2

Reference yield:

: 99208-71-6
(5S)-1-aza-2,2-dimethyl-3-oxa-8-oxo-bicyclo[3.3.0]octane

: 212890-91-0
(S)-(-)-tert-butyl 4,4-bisbenzyl-2-(hydroxymethyl)pyrrolidinecarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 73 percent / LDA; HMPA / tetrahydrofuran / 5.5 h / -78 °C

2: 97 percent / p-TsOH / methanol / 1 h / Heating

3: 95 percent / LiAlH₄ / tetrahydrofuran / 96 h / 0 - 20 °C

4: 84 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; 1: Alkylation / 2: Ring cleavage / 3: Reduction / 4: Carboxylation;
DOI:10.1016/S0040-4020(98)00485-2