(3S,5S)-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxotetrahydro-furan-2-yl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (3S,5S)-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxotetrahydro-furan-2-yl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 934841-17-5
• Molecular Formula: C19H31NO5
• Molecular Weight: 353.459
• Mol file: 934841-17-5.mol

Synonyms:(3S,5S)-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxotetrahydro-furan-2-yl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester;(3S,5S)-3-(1-Methylethyl)-2-oxo-5-[(2S,4S)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]-1-pyrrolidinecarboxylic acid tert-butyl ester;(3S,5S)-tert-Butyl 3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-2-oxopyrrolidine-1-carboxylate;

Chemical Property of (3S,5S)-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxotetrahydro-furan-2-yl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

• PSA: 72.91000
• Density: 1.112
• LogP: 3.32020
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

(3S,5S)-tert-Butyl 3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-2-oxopyrrolidine-1-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,5S)-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxotetrahydro-furan-2-yl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester

There total 7 articles about (3S,5S)-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxotetrahydro-furan-2-yl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester 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:

(3S,5S)-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)pyrrolidin-2-one (934841-30-2) + di-tert-butyl dicarbonate (24424-99-5) → (3S,5S)-tert-butyl-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-2-oxopyrrolidine-1-carboxylate (934841-17-5)

Guidance literature:

(3S,5S)-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)pyrrolidin-2-one; With dmap; triethylamine; In Isopropyl acetate; at 40 - 45 ℃;

di-tert-butyl dicarbonate; In Isopropyl acetate; at 40 - 45 ℃;

Reference yield:

[(4S)-2-hydroxy-4-hydroxymethyl-1-(2-hydroxymethyl-3-methyl-butyl)-5-methyl-hexyl]-carbamic acid tert-butyl ester (1068437-95-5) → (3S,5S)-tert-butyl-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-2-oxopyrrolidine-1-carboxylate (934841-17-5)

Guidance literature:

With 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate; In dichloromethane; acetonitrile; at 20 ℃; Product distribution / selectivity; Molecular sieve; Heating / reflux;

Reference yield:

isopentanoyl chloride (108-12-3) → (3S,5S)-tert-butyl-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-2-oxopyrrolidine-1-carboxylate (934841-17-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-butyllithium / tetrahydrofuran / 1.5 h / -30 - -25 °C / Inert atmosphere

1.2: 1.5 h / -25 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -50 °C / Inert atmosphere; Large scale

2.2: 2 h / -50 °C / Inert atmosphere; Large scale

2.3: 3.5 h / -50 - 10 °C / Inert atmosphere; Large scale

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / 0 °C / Large scale

4.1: lithium bromide; magnesium(II) perchlorate / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere

5.1: Aliquat 336; sodium azide / N,N-dimethyl-formamide / 24 h / 75 °C / Inert atmosphere; Large scale

6.1: 5%-palladium/activated carbon; hydrogen / toluene / 24 h / 20 °C / 15001.5 Torr / Autoclave; Large scale

6.2: 1 h / 0 °C / Large scale

7.1: dmap; triethylamine / ethyl acetate / 12 h / 50 °C / Large scale

With dmap; n-butyllithium; sodium azide; magnesium(II) perchlorate; 5%-palladium/activated carbon; hydrogen; Aliquat 336; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/acs.oprd.5b00009

upstream raw materials:

[(4S)-2-hydroxy-4-hydroxymethyl-1-(2-hydroxymethyl-3-methyl-butyl)-5-methyl-hexyl]-carbamic acid tert-butyl ester

(3S,5S)-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)pyrrolidin-2-one

di-tert-butyl dicarbonate

isopentanoyl chloride

Downstream raw materials:

C₃₀H₄₇NO₈

tert-butyl {(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate