3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzy1 ester 1-tert-butyl ester

Base Information

• Chemical Name: 3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzy1 ester 1-tert-butyl ester
• CAS No.: 1257235-25-8
• Molecular Formula: C₂₆H₃₁FN₂O₅
• Molecular Weight: 470.541
• Mol file: 1257235-25-8.mol

Synonyms:3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzy1 ester 1-tert-butyl ester

Chemical Property of 3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzy1 ester 1-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzy1 ester 1-tert-butyl ester

There total 18 articles about 3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzy1 ester 1-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: 94.0%

(-)-(3S,3aS,6aR)-3-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (648930-90-9) + 4-Fluorobenzyl bromide (459-46-1) → 3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzy1 ester 1-tert-butyl ester (1257235-25-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃;

Reference yield:

N-Boc-4R-O-TBS-2R-aminoethyl-pyrrolidine (1245724-76-8) → 3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzy1 ester 1-tert-butyl ester (1257235-25-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: dichloromethane / 0 - 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C

3.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 0 - 20 °C

4.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C

5.1: borane / tetrahydrofuran / -30 - 0 °C

5.2: -10 - 0 °C

6.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 0 °C

7.1: hydrogen / palladium 10% on activated carbon / methanol / 3 h

8.1: sodium acetate / 85 - 90 °C

9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

10.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C

11.1: di-isopropyl azodicarboxylate; triphenylphosphine / benzene / 20 °C

12.1: sodium hydroxide / tetrahydrofuran; methanol / 0 °C

13.1: sodium hydride / N,N-dimethyl-formamide / 0 °C

With di-isopropyl azodicarboxylate; borane; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; sodium hydride; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium hydroxide; dmap; palladium 10% on activated carbon; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

Reference yield:

4-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-vinyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (137934-80-6) → 3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzy1 ester 1-tert-butyl ester (1257235-25-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: sodium tetrahydroborate / tetrahydrofuran; water / -20 °C

2.1: hydrogen / Raney nickel / ethanol; water / 1 h / 2844.39 Torr

3.1: dichloromethane / 0 - 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C

5.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 0 - 20 °C

6.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C

7.1: borane / tetrahydrofuran / -30 - 0 °C

7.2: -10 - 0 °C

8.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 0 °C

9.1: hydrogen / palladium 10% on activated carbon / methanol / 3 h

10.1: sodium acetate / 85 - 90 °C

11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

12.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C

13.1: di-isopropyl azodicarboxylate; triphenylphosphine / benzene / 20 °C

14.1: sodium hydroxide / tetrahydrofuran; methanol / 0 °C

15.1: sodium hydride / N,N-dimethyl-formamide / 0 °C

With sodium tetrahydroborate; di-isopropyl azodicarboxylate; borane; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; sodium hydride; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium hydroxide; dmap; palladium 10% on activated carbon; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

upstream raw materials:

(-)-(3S,3aS,6aR)-3-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

4-Fluorobenzyl bromide

N-Boc-4R-O-TBS-2R-aminoethyl-pyrrolidine

4-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-vinyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

4-(2-amino-3,3-dimethyl-butyryl)-3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

4-(2-benzyloxycarbonylamino-3,3-dimethyl-butyryl)-3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

(1-{1-[6-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester