(2S,4R)-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Base Information

• Chemical Name: (2S,4R)-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
• CAS No.: 127767-87-7
• Molecular Formula: C₁₆H₂₂N₂O₉S
• Molecular Weight: 418.425
• Mol file: 127767-87-7.mol

Synonyms:(2S,4R)-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Chemical Property of (2S,4R)-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

There total 13 articles about (2S,4R)-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine 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: 89.0%

→ (2S,4R)-1-benzyloxycarbonyl-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxypyrrolidine (127768-04-1) + (2S,4R)-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (127767-87-7)

Guidance literature:

Reference yield:

(2S,4R)-2-(carboxymethyloxymethyl)-4-methanesulfonyl-oxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine + isobutyl chloroformate (543-27-1) → (2S,4R)-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (127767-87-7)

Guidance literature:

With sodium borohydrid; triethylamine; In tetrahydrofuran; methanol; chloroform; water; acetic acid; ethyl acetate;

Reference yield:

(2S,4R)-4-hydroxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (101803-29-6) → (2S,4R)-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (127767-87-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 100 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

2: 48 percent / NaBH₄ / ethanol / 16 h / Ambient temperature

3: H₂ / 20percent Pd(OH)2/C / methanol / 3 h / 760 Torr / Ambient temperature

4: aq. NaOH / tetrahydrofuran / 2 h

5: 94 percent / NaH / tetrahydrofuran / 3 h / Ambient temperature

6: aq. 6N HCl / 3 h / Heating

7: 4N aq. NaOH / tetrahydrofuran; H₂O / 2 h

8: 75 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

9: Et₃N / tetrahydrofuran / 0.5 h / -10 - -5 °C

10: NaBH₄ / tetrahydrofuran / 1 h

With 1H-imidazole; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; hydrogen; sodium hydride; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(97)00142-9

upstream raw materials:

(2S,4R)-4-t-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine

(2S,4R)-2-carboxymethyloxymethyl-4-hydroxypyrrolidine

(6S,8R)-8-t-butyldimethylsilyloxy-2-oxo-1-aza-4-oxabicyclo[4.3.0]nonane

(2S,4R)-4-t-butyldimethylsilyloxy-1-chloroacetyl-2-(hydroxymethyl)pyrrolidine

Downstream raw materials:

(2S,4S)-4-Acetylsulfanyl-2-(2-hydroxy-ethoxymethyl)-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

(4R,5S,6S)-3-[(3S,5S)-5-(2-Hydroxy-ethoxymethyl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester