(2S,3R)-tert-butyl 2-(hydroxymethyl)-3-(4-(hydroxymethyl)phenyl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:(2S,3R)-tert-butyl 2-(hydroxymethyl)-3-(4-(hydroxymethyl)phenyl)pyrrolidine-1-carboxylate
CAS No.:1622154-07-7
Molecular Formula:C₁₇H₂₅NO₄
Molecular Weight:307.39
Hs Code.:

Synonyms:(2S,3R)-tert-butyl 2-(hydroxymethyl)-3-(4-(hydroxymethyl)phenyl)pyrrolidine-1-carboxylate

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Chemical Property of (2S,3R)-tert-butyl 2-(hydroxymethyl)-3-(4-(hydroxymethyl)phenyl)pyrrolidine-1-carboxylate

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Technology Process of (2S,3R)-tert-butyl 2-(hydroxymethyl)-3-(4-(hydroxymethyl)phenyl)pyrrolidine-1-carboxylate

There total 8 articles about (2S,3R)-tert-butyl 2-(hydroxymethyl)-3-(4-(hydroxymethyl)phenyl)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: 88.0%

: 1622154-06-6
(2S,3R)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(4-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)pyrrolidine-1-carboxylate

: 1622154-07-7
(2S,3R)-tert-butyl 2-(hydroxymethyl)-3-(4-(hydroxymethyl)phenyl)pyrrolidine-1-carboxylate

Guidance literature:: (2S,3R)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(4-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)pyrrolidine-1-carboxylate; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere;

With water; sodium hydrogencarbonate; In tetrahydrofuran; ethyl acetate;

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 1622154-07-7
(2S,3R)-tert-butyl 2-(hydroxymethyl)-3-(4-(hydroxymethyl)phenyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1H-imidazole / dichloromethane / 24 h / 20 °C

2.1: dmap / acetonitrile / 16 h / 20 °C

3.1: lithium hexamethyldisilazane; Phenylselenyl chloride / tetrahydrofuran / -78 °C

3.2: 0 - 20 °C

4.1: tert.-butyl lithium / diethyl ether / 0.58 h / -78 °C / Inert atmosphere

4.2: 1.92 h / -78 - -42 °C / Inert atmosphere

5.1: borane-THF / tetrahydrofuran / 18 h / Reflux; Inert atmosphere

5.2: 2 h / 0 °C

5.3: 2.5 h / 0 - 20 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; Phenylselenyl chloride; borane-THF; tetrabutyl ammonium fluoride; tert.-butyl lithium; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

Reference yield:

: 81658-27-7
(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

: 1622154-07-7
(2S,3R)-tert-butyl 2-(hydroxymethyl)-3-(4-(hydroxymethyl)phenyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: tert.-butyl lithium / diethyl ether / 0.58 h / -78 °C / Inert atmosphere

1.2: 1.92 h / -78 - -42 °C / Inert atmosphere

2.1: borane-THF / tetrahydrofuran / 18 h / Reflux; Inert atmosphere

2.2: 2 h / 0 °C

2.3: 2.5 h / 0 - 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

With borane-THF; tetrabutyl ammonium fluoride; tert.-butyl lithium; In tetrahydrofuran; diethyl ether;