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

Base Information

• Chemical Name: (2S,5S)-tert-butyl 2-(hydroxydiphenylmethyl)-5-(naphthalen-2-yl)pyrrolidine-1-carboxylate
• CAS No.: 1552271-79-0
• Molecular Formula: C₃₂H₃₃NO₃
• Molecular Weight: 479.619

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

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

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

There total 2 articles about (2S,5S)-tert-butyl 2-(hydroxydiphenylmethyl)-5-(naphthalen-2-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: 41.0%

(2S,5S)-1-tert-butyl 2-methyl 5-(naphthalen-2-yl)pyrrolidine-1,2-dicarboxylate (1552271-25-6) + phenylmagnesium bromide (100-58-3) → (2S,5S)-tert-butyl 2-(hydroxydiphenylmethyl)-5-(naphthalen-2-yl)pyrrolidine-1-carboxylate (1552271-79-0)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1021/ja4129394

Reference yield:

1-tert-butyl 2-methyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate (195964-54-6) → (2S,5S)-tert-butyl 2-(hydroxydiphenylmethyl)-5-(naphthalen-2-yl)pyrrolidine-1-carboxylate (1552271-79-0)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 16 h / -78 - 4 °C / Inert atmosphere

2.1: tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ja4129394

Reference yield: 99.0%

(2S,5S)-tert-butyl 2-(hydroxydiphenylmethyl)-5-(naphthalen-2-yl)pyrrolidine-1-carboxylate (1552271-79-0) → [(2S,5S)-5-(naphthalen-2-yl)pyrrolidin-2-yl]diphenylmethanol (1552271-29-0)

Guidance literature:

With sodium hydroxide; In ethanol; at 20 ℃; for 20h; Inert atmosphere; Reflux;

DOI:10.1021/ja4129394

upstream raw materials:

1-tert-butyl 2-methyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate

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

phenylmagnesium bromide

Downstream raw materials:

[(2S,5S)-5-(naphthalen-2-yl)pyrrolidin-2-yl]diphenylmethanol

((2S,2'S,5S,5'S)-1,1'-((2-hydroxy-5-methyl-1,3-phenylene)-bis-(methylene))-bis-(5-(naphthalen-2-yl)pyrrolidine-2,1-diyl))-bis-(diphenylmethanol)

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