(2S,3R)-1-(tert-butoxycarbonyl)-3-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,3R)-1-(tert-butoxycarbonyl)-3-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-pyrrolidine-2-carboxylic acid
• CAS No.: 1622235-83-9
• Molecular Formula: C₂₀H₂₇NO₆
• Molecular Weight: 377.437

Synonyms:(2S,3R)-1-(tert-butoxycarbonyl)-3-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-pyrrolidine-2-carboxylic acid

Chemical Property of (2S,3R)-1-(tert-butoxycarbonyl)-3-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-pyrrolidine-2-carboxylic acid

Chemical Property:

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Technology Process of (2S,3R)-1-(tert-butoxycarbonyl)-3-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-pyrrolidine-2-carboxylic acid

There total 1 articles about (2S,3R)-1-(tert-butoxycarbonyl)-3-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-pyrrolidine-2-carboxylic acid 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:

(S)-Pyroglutaminol (17342-08-4) → (2S,3R)-1-(tert-butoxycarbonyl)-3-(2,2-dimethyl-4-oxo-4H-benzo-[d][1,3]dioxin-6-yl)pyrrolidine-2-carboxylic acid (1622235-82-8) + (2S,3R)-1-(tert-butoxycarbonyl)-3-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-pyrrolidine-2-carboxylic acid (1622235-83-9)

Guidance literature:

Multi-step reaction with 7 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 / pentane; diethyl ether / 0.58 h / -78 °C / Inert atmosphere

4.2: 0.25 h / -78 - -42 °C / Inert atmosphere

4.3: 1 h / -78 - -42 °C / Inert atmosphere

5.1: borane-THF / tetrahydrofuran / 3.5 h / 80 °C / Inert atmosphere

5.2: 3.5 h / 0 - 20 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

6.2: Inert atmosphere

7.1: sodium periodate; ruthenium(III) trichloride hydrate / water; ethyl acetate; acetonitrile / 1.5 h / 0 °C

With 1H-imidazole; dmap; sodium periodate; borane-THF; ruthenium(III) trichloride hydrate; tetrabutyl ammonium fluoride; tert.-butyl lithium; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile; pentane;

Reference yield:

1,3-dibromobenzene (108-36-1) + (2S,3R)-1-(tert-butoxycarbonyl)-3-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-pyrrolidine-2-carboxylic acid (1622235-83-9) → (2S,3R)-tert-butyl 3-(3-bromophenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidine-1-carboxylate

Guidance literature:

1,3-dibromobenzene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.333333h;

With copper(l) cyanide; In tetrahydrofuran; at -78 - -50 ℃; for 0.333333h;

(2S,3R)-1-(tert-butoxycarbonyl)-3-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-pyrrolidine-2-carboxylic acid; With chloro-trimethyl-silane; In tetrahydrofuran; at -78 - -50 ℃; for 1.33333h;

DOI:10.1021/acs.jmedchem.5b00750

Reference yield:

(2S,3R)-1-(tert-butoxycarbonyl)-3-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-pyrrolidine-2-carboxylic acid (1622235-83-9) → (2S,3R)-N-(tert-butoxycarbonyl)-2-[[(tert-butyl)dimethylsilyloxy]-methyl]-3-(3-bromophenyl)pyrrolidine

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C

1.2: 0.33 h / -78 - -50 °C

1.3: 1.33 h / -78 - -50 °C

2.1: borane-THF / tetrahydrofuran / 20 h / Reflux

2.2: 1.33 h / 0 - 20 °C

With n-butyllithium; borane-THF; In tetrahydrofuran;

DOI:10.1021/acs.jmedchem.5b00750

upstream raw materials:

(S)-Pyroglutaminol

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