(2R,3S,4R)-benzyl 4-fluoro-2-(hydroxymethyl)-3-methylpyrrolidine-1-carboxylate

Base Information

Chemical Name:(2R,3S,4R)-benzyl 4-fluoro-2-(hydroxymethyl)-3-methylpyrrolidine-1-carboxylate
CAS No.:1610036-77-5
Molecular Formula:C₁₄H₁₈FNO₃
Molecular Weight:267.3
Hs Code.:

Synonyms:(2R,3S,4R)-benzyl 4-fluoro-2-(hydroxymethyl)-3-methylpyrrolidine-1-carboxylate

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Chemical Property of (2R,3S,4R)-benzyl 4-fluoro-2-(hydroxymethyl)-3-methylpyrrolidine-1-carboxylate

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Technology Process of (2R,3S,4R)-benzyl 4-fluoro-2-(hydroxymethyl)-3-methylpyrrolidine-1-carboxylate

There total 6 articles about (2R,3S,4R)-benzyl 4-fluoro-2-(hydroxymethyl)-3-methylpyrrolidine-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: 53.0%

: 1610036-76-4
(2R,3S,4R)-1-benzyl 2-methyl 4-fluoro-3-methylpyrrolidine-1,2-dicarboxylate

: 1610036-77-5
(2R,3S,4R)-benzyl 4-fluoro-2-(hydroxymethyl)-3-methylpyrrolidine-1-carboxylate

Guidance literature:: With lithium borohydride; In tetrahydrofuran; at 0 - 20 ℃; for 16h;

Reference yield:

: 1367552-62-2
1-benzyl 2-methyl (R)-4-((tert-butyldimethylsilyl)oxy)-4.5-dihydro-1H-pyrrole-1,2-dicarboxylate

: 1610036-77-5
(2R,3S,4R)-benzyl 4-fluoro-2-(hydroxymethyl)-3-methylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: copper(I) bromide dimethylsulfide complex / diethyl ether / 1 h

1.2: 0.75 h / -45 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1.08 h / 20 °C

4.1: lithium hydroxide monohydrate / methanol; tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere

4.2: 16 h / 20 °C

5.1: diethylamino-sulfur trifluoride / dichloromethane / 16 h / -78 - 20 °C

6.1: lithium borohydride / tetrahydrofuran / 16 h / 0 - 20 °C

With lithium borohydride; copper(I) bromide dimethylsulfide complex; lithium hydroxide monohydrate; diethylamino-sulfur trifluoride; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

Reference yield:

: 1367552-64-4
(2R,3S,4R)-1-benzyl 2-methyl 4-((tert-butyldimethylsilyl)oxy)-3-methylpyrrolidine-1,2-dicarboxylate

: 1610036-77-5
(2R,3S,4R)-benzyl 4-fluoro-2-(hydroxymethyl)-3-methylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

2.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1.08 h / 20 °C

3.1: lithium hydroxide monohydrate / methanol; tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere

3.2: 16 h / 20 °C

4.1: diethylamino-sulfur trifluoride / dichloromethane / 16 h / -78 - 20 °C

5.1: lithium borohydride / tetrahydrofuran / 16 h / 0 - 20 °C

With lithium borohydride; lithium hydroxide monohydrate; diethylamino-sulfur trifluoride; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water;