(2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester
• CAS No.: 344791-02-2
• Molecular Formula: C₂₂H₂₇NO₄
• Molecular Weight: 369.461

Synonyms:(2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester

Chemical Property of (2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester

There total 6 articles about (2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester 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%

di-tert-butyl dicarbonate (24424-99-5) + trans-4-hydroxy-α,α-diphenyl-L-prolinol hydrochloride (1173184-14-9) → (2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester (344791-02-2)

Guidance literature:

With triethylamine; In dichloromethane; for 1h; Reflux;

DOI:10.1016/j.molcata.2014.12.009

Reference yield: 85.8%

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) + phenylmagnesium bromide (100-58-3) → (2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester (344791-02-2)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 3.5h; Inert atmosphere;

DOI:10.1021/acs.oprd.0c00268

Reference yield: 82.0%

phenylmagnesium chloride (100-59-4) + 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → (2S,4R)-4-hydroxy-2-(1-hydroxy-1,1-diphenylmethyl)pyrroline-1-carboxylic acid tert-butyl ester (344791-02-2)

Guidance literature:

In tetrahydrofuran;

DOI:10.1055/s-2008-1067146

upstream raw materials:

phenylmagnesium chloride

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

phenylmagnesium bromide

di-tert-butyl dicarbonate

Downstream raw materials:

3-(5-((3R,5S)-5-(hydroxydiphenylmethyl)pyrrolidin-3-yloxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide

(6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one

((2S,4R)-diphenyl-4-(prop-2-yn-1-yloxy)pyrrolidin-2-yl)methanol

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