(S)-3-((R)-hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid t-butyl ester

Base Information

• Chemical Name: (S)-3-((R)-hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid t-butyl ester
• CAS No.: 1204677-42-8
• Molecular Formula: C₁₆H₂₃NO₃
• Molecular Weight: 277.364
• Mol file: 1204677-42-8.mol

Synonyms:(S)-3-((R)-hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid t-butyl ester

Chemical Property of (S)-3-((R)-hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid t-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (S)-3-((R)-hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid t-butyl ester

There total 2 articles about (S)-3-((R)-hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid t-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:

phenylmagnesium bromide (100-58-3) + (S)-3-formylpyrrolidine-1-carboxylic acid t-butyl ester (191348-04-6) → 1,1-dimethylethyl (3S)-3-[(S)-hydroxyphenylmethyl]-1-pyrrolidinecarboxylate (1204677-43-9) + (S)-3-((R)-hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid t-butyl ester (1204677-42-8)

Guidance literature:

phenylmagnesium bromide; (S)-3-formylpyrrolidine-1-carboxylic acid t-butyl ester; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran;

Reference yield:

tert-butyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate (199174-24-8) → (S)-3-((R)-hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid t-butyl ester (1204677-42-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate / dichloromethane; water / 0.17 h / 0 °C

2: tetrahydrofuran / -78 - 20 °C / Inert atmosphere

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.bmcl.2012.12.061

Reference yield:

(S)-3-((R)-hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid t-butyl ester (1204677-42-8) + 4-chloro-2-fluoro-1-iodobenzene (6797-79-1) → BOC-(S)-3-[(R)-(4-chloro-2-fluorophenoxy)phenylmethyl]pyrrolidine (1204677-51-9)

Guidance literature:

With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In toluene; at 105 ℃; for 48h;

upstream raw materials:

phenylmagnesium bromide

(S)-3-formylpyrrolidine-1-carboxylic acid t-butyl ester

tert-butyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate

Downstream raw materials:

BOC-(S)-3-[(R)-(4-chloro-2-fluorophenoxy)phenylmethyl]pyrrolidine

BOC-(S)-3-[(R)-(2-methanesulfonylphenoxy)phenylmethyl]pyrrolidine

(S)-3-[(R)-(2,4-difluorophenoxy)phenylmethyl]pyrrolidine trifluoroacetate