5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(3-aminophenyl)-6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aS,4S,6R,6aR)-

Base Information

• Chemical Name: 5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(3-aminophenyl)-6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aS,4S,6R,6aR)-
• CAS No.: 188744-91-4
• Molecular Formula: C25H42 N2 O5 Si
• Molecular Weight: 478.7
• Mol file: 188744-91-4.mol

Synonyms:5H-1,3-Dioxolo[4,5-c]pyrrole-5-carboxylicacid,4-(3-aminophenyl)-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]tetrahydro-2,2-dimethyl-,1,1-dimethylethyl ester, [3aS-(3aa,4a,6a,6aa)]-

Chemical Property of 5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(3-aminophenyl)-6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aS,4S,6R,6aR)-

Chemical Property:

• PSA: 83.25000
• LogP: 5.99020

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(3-aminophenyl)-6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aS,4S,6R,6aR)-

There total 7 articles about 5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(3-aminophenyl)-6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aS,4S,6R,6aR)- 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: 66.0%

(3aR,4R,6S,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(3-diallylamino-phenyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester (188744-89-0) → (3aS,4S,6R,6aR)-4-(3-Amino-phenyl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester (188744-91-4)

Guidance literature:

With Wilkinson's catalyst; In water; acetonitrile; for 4h; Heating;

DOI:10.1016/S0040-4020(96)01172-6

Reference yield:

(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole (153172-31-7) → (3aS,4S,6R,6aR)-4-(3-Amino-phenyl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester (188744-91-4)

Guidance literature:

Multi-step reaction with 5 steps

1: NCS / pentane / 0.5 h / Ambient temperature

2: 1.) BuLi, 2,2,6,6-tetramethylpiperidine / 1.) THF, 0 deg C, 2.) THF, -78 deg C

3: 58 percent / tetrahydrofuran; diethyl ether; hexane / 1.) -78 deg C, 30 min, 2.) room temperature, 30 min

4: 99 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) room temperature, 3 h

5: 66 percent / (Ph₃P)3RhCl / acetonitrile; H₂O / 4 h / Heating

With 2,2,6,6-tetramethyl-piperidine; N-chloro-succinimide; Wilkinson's catalyst; n-butyllithium; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetonitrile; pentane;

DOI:10.1016/S0040-4020(96)01172-6

Reference yield:

(3aR,4R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-chloro-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole (153172-32-8) → (3aS,4S,6R,6aR)-4-(3-Amino-phenyl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester (188744-91-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) BuLi, 2,2,6,6-tetramethylpiperidine / 1.) THF, 0 deg C, 2.) THF, -78 deg C

2: 58 percent / tetrahydrofuran; diethyl ether; hexane / 1.) -78 deg C, 30 min, 2.) room temperature, 30 min

3: 99 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) room temperature, 3 h

4: 66 percent / (Ph₃P)3RhCl / acetonitrile; H₂O / 4 h / Heating

With 2,2,6,6-tetramethyl-piperidine; Wilkinson's catalyst; n-butyllithium; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4020(96)01172-6

upstream raw materials:

(3aR,4R,6S,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(3-diallylamino-phenyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

(3aR,4R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-chloro-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole

(3aR,4R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole

Downstream raw materials:

(3aR,4R,6S,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-6-(3-nitro-phenyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

Refernces