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147254-64-6

Basic Information
CAS No.: 147254-64-6
Name: (3R)-2'-(4-Bromo-2-fluorobenzyl)spiro[pyrrolidine-3,4'-1'H-pyrrolo[1,2-a]pyrazine]-1',2,3',5(2'H)-tetraone
Article Data: 6
Molecular Structure:
Molecular Structure of 147254-64-6 ((3R)-2'-(4-Bromo-2-fluorobenzyl)spiro[pyrrolidine-3,4'-1'H-pyrrolo[1,2-a]pyrazine]-1',2,3',5(2'H)-tetraone)
Formula: C17H11 Br F N3 O4
Molecular Weight: 420.194
Synonyms: Spiro[pyrrolidine-3,4'(1'H)-pyrrolo[1,2-a]pyrazine]-1',2,3',5(2'H)-tetrone,2'-[(4-bromo-2-fluorophenyl)methyl]-, (-)-;Spiro[pyrrolidine-3,4'(1'H)-pyrrolo[1,2-a]pyrazine]-1',2,3',5(2'H)-tetrone,2'-[(4-bromo-2-fluorophenyl)methyl]-, (3'R)- (9CI);(3R)-2'-(4-Bromo-2-fluorobenzyl)-1',2',3',4'-tetrahydrospiro[pyrrolidine-3,4'-pyrrolo[1,2-a]pyrazine]-1',2,3',5-tetraone;AS 3201; Ranirestat
Density: 1.83g/cm3
Melting Point: 192-193℃
Boiling Point: 702.7°Cat760mmHg
Flash Point: 378.8°C
PSA: 91.97000
LogP: 1.52790
Synthetic route
1211939-75-1

(S)-methyl 4-(2-amino-2-oxoethyl)-2-(4-bromo-2-fluorobenzyl)-1,3-dioxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-carboxylate

147254-64-6

ranirestat

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; Inert atmosphere;95%
112734-22-2

4-bromo-2-fluorobenzylamine

159213-26-0

R-(-)-3-ethoxycarbonyl-3-(2-(trichloroacetyl)pyrrol-1-yl)pyrrolidin-2,5-dione

147254-64-6

ranirestat

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 5h;71%
With triethylamine In N,N-dimethyl-formamide at 20℃;65%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 8h;65%
1000784-39-3

(2R)-2-ethoxycarbonyl-2-(pyrrol-1-yl)succinimide diisopropylamine salt

112734-22-2

4-bromo-2-fluorobenzylamine

147254-64-6

ranirestat

Conditions
ConditionsYield
Stage #1: (2R)-2-ethoxycarbonyl-2-(pyrrol-1-yl)succinimide diisopropylamine salt With sulfuric acid; water In ethyl acetate
Stage #2: With trifluoroacetyl chloride In ethyl acetate for 6h; Heating / reflux;
Stage #3: 4-bromo-2-fluorobenzylamine With water; sodium hydrogencarbonate; diisopropylamine more than 3 stages;
58%

(4-bromo-2-fluorophenyl)methanamine hydrochloride

159213-26-0

R-(-)-3-ethoxycarbonyl-3-(2-(trichloroacetyl)pyrrol-1-yl)pyrrolidin-2,5-dione

147254-64-6

ranirestat

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature;45%
159213-18-0

(R)-ethyl-3-amino-2,5-dioxopyrrolidine-3-carboxylate

147254-64-6

ranirestat

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 72.4 percent / AcOH / 1.5 h / 70 °C
2: 91.9 percent / CHCl3 / 16 h / Heating
3: 45 percent / Et3N / dimethylformamide / 16 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1.1: water / Heating
1.2: 22; 13 / 12 h / 40 °C
2.1: 10 h / 80 °C
3.1: N,N-dimethyl-formamide / 5 h / 20 °C
View Scheme
159213-19-1

ethyl 2,5-dioxo-3-(1H-pyrrol-1-yl)pyrrolidine-3-carboxylate

147254-64-6

ranirestat

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91.9 percent / CHCl3 / 16 h / Heating
2: 45 percent / Et3N / dimethylformamide / 16 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: ethyl acetate / Reflux
2: triethylamine / N,N-dimethyl-formamide / 8 h / 20 °C
View Scheme
147194-10-3

ethyl 3-benzyloxycarbonylamino-2,5-dioxopyrrolidine-3-carboxylate

147254-64-6

ranirestat

Conditions
ConditionsYield
Multi-step reaction with 5 steps
2: 95.9 percent / H2 / 5percent Pd/C / ethanol / 40 - 50 °C / 760 Torr
3: 72.4 percent / AcOH / 1.5 h / 70 °C
4: 91.9 percent / CHCl3 / 16 h / Heating
5: 45 percent / Et3N / dimethylformamide / 16 h / Ambient temperature
View Scheme
159213-17-9

(R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide

147254-64-6

ranirestat

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95.9 percent / H2 / 5percent Pd/C / ethanol / 40 - 50 °C / 760 Torr
2: 72.4 percent / AcOH / 1.5 h / 70 °C
3: 91.9 percent / CHCl3 / 16 h / Heating
4: 45 percent / Et3N / dimethylformamide / 16 h / Ambient temperature
View Scheme
952656-32-5

ethyl (R)-3-hydrazinyl-2,5-dioxopyrrolidine-3-carboxylate hydrochloride

147254-64-6

ranirestat

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogen / nickel / ethanol / 42 h / 20 °C
2.1: water / Heating
2.2: 22; 13 / 12 h / 40 °C
3.1: 10 h / 80 °C
4.1: N,N-dimethyl-formamide / 5 h / 20 °C
View Scheme

R-(-)-3-ethoxycarbonyl-3-(N,N'-di(tert-butoxycarbonyl)hydrazino)pyrrolidin-2,5-dione hydrochloride

147254-64-6

ranirestat

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogenchloride / toluene / 2.5 h / 0 °C
2.1: hydrogen / nickel / ethanol / 42 h / 20 °C
3.1: water / Heating
3.2: 22; 13 / 12 h / 40 °C
4.1: 10 h / 80 °C
5.1: N,N-dimethyl-formamide / 5 h / 20 °C
View Scheme
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