(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(hydroxymethyl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

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Chemical Name:(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(hydroxymethyl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate
CAS No.:1622235-80-6
Molecular Formula:C₂₄H₃₁NO₅
Molecular Weight:413.514
Hs Code.:

Synonyms:(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(hydroxymethyl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

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Chemical Property of (2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(hydroxymethyl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

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Technology Process of (2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(hydroxymethyl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

There total 12 articles about (2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(hydroxymethyl)phenyl)-2-(hydroxymethyl)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: 92.0%

: 1622235-76-0
(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-pyrrolidine-1-carboxylate

: 1622235-80-6
(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(hydroxymethyl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Guidance literature:: (2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-pyrrolidine-1-carboxylate; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 18h;

With water; sodium hydrogencarbonate; In tetrahydrofuran;

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 1622235-80-6
(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(hydroxymethyl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

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

2.1: dmap / acetonitrile / 0 - 20 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

3.2: 0.75 h / -78 °C

3.3: 1.41 h / 0 - 20 °C

4.1: tert.-butyl lithium / diethyl ether / 0.75 h / -78 °C / Inert atmosphere

4.2: 0.42 h / -78 - -42 °C / Inert atmosphere

5.1: borane-THF / tetrahydrofuran / 20.08 h / Inert atmosphere; Reflux

5.2: 0.5 h / 0 °C / Inert atmosphere

5.3: 1.33 h / 20 °C / Inert atmosphere

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

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

Reference yield:

: 81658-26-6
tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate

: 1622235-80-6
(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(hydroxymethyl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

1.2: 0.75 h / -78 °C

1.3: 1.41 h / 0 - 20 °C

2.1: tert.-butyl lithium / diethyl ether / 0.75 h / -78 °C / Inert atmosphere

2.2: 0.42 h / -78 - -42 °C / Inert atmosphere

3.1: borane-THF / tetrahydrofuran / 20.08 h / Inert atmosphere; Reflux

3.2: 0.5 h / 0 °C / Inert atmosphere

3.3: 1.33 h / 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C

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