(2S,5S)-tert-butyl 2-(hydroxydiphenylmethyl)-5-(naphthalen-1-yl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:(2S,5S)-tert-butyl 2-(hydroxydiphenylmethyl)-5-(naphthalen-1-yl)pyrrolidine-1-carboxylate
CAS No.:1552271-77-8
Molecular Formula:C₃₂H₃₃NO₃
Molecular Weight:479.619
Hs Code.:

Synonyms:(2S,5S)-tert-butyl 2-(hydroxydiphenylmethyl)-5-(naphthalen-1-yl)pyrrolidine-1-carboxylate

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Chemical Property of (2S,5S)-tert-butyl 2-(hydroxydiphenylmethyl)-5-(naphthalen-1-yl)pyrrolidine-1-carboxylate

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Technology Process of (2S,5S)-tert-butyl 2-(hydroxydiphenylmethyl)-5-(naphthalen-1-yl)pyrrolidine-1-carboxylate

There total 5 articles about (2S,5S)-tert-butyl 2-(hydroxydiphenylmethyl)-5-(naphthalen-1-yl)pyrrolidine-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: 94.0%

: 1-tert-butyl 2-methyl 5-(naphthalen-1-yl)pyrrolidine-1,2-dicarboxylate

: 100-58-3
phenylmagnesium bromide

: 1552271-77-8
(2S,5S)-tert-butyl 2-(hydroxydiphenylmethyl)-5-(naphthalen-1-yl)pyrrolidine-1-carboxylate

Guidance literature:: In tetrahydrofuran; at 20 ℃; for 6h; Inert atmosphere;
DOI:10.1021/ja4129394

Reference yield: 83.0%

: 1552271-24-5
(2S,5S)-1-tert-butyl 2-methyl 5-(naphthalen-1-yl)pyrrolidine-1,2-dicarboxylate

: 100-58-3
phenylmagnesium bromide

: 1552271-77-8
(2S,5S)-tert-butyl 2-(hydroxydiphenylmethyl)-5-(naphthalen-1-yl)pyrrolidine-1-carboxylate

Guidance literature:: In tetrahydrofuran; at 0 - 20 ℃; for 12h; Inert atmosphere;
DOI:10.1002/anie.201509302

Reference yield:

: 108963-96-8
(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

: 1552271-77-8
(2S,5S)-tert-butyl 2-(hydroxydiphenylmethyl)-5-(naphthalen-1-yl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium triethylborohydride / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / 20 °C / Inert atmosphere

3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran; diethyl ether / 1 h / -40 °C / Inert atmosphere

3.2: -78 - 0 °C / Inert atmosphere

4.1: tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere

With copper(I) bromide dimethylsulfide complex; lithium triethylborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether;
DOI:10.1002/anie.201509302