Product Name

Synthetic route

(5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester
178172-26-4

(5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
With sodium isopropylate; formamide In diethyl ether at 20℃; for 2.16667h; Solvent; Temperature; Cooling with ice;93%
With Candida antarctica lipase B; ammonium carbamate; Ascarite; calcium chloride at 50℃; for 72h; Product distribution; Kinetics; Further Variations:; Reagents; Temperatures;81%
Multi-step reaction with 2 steps
1: water; lithium hydroxide / ethanol
2: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
View Scheme
N-BOC dehydroproline DIPEA

N-BOC dehydroproline DIPEA

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Stage #1: N-BOC dehydroproline DIPEA With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -25 - -20℃; for 2h;
Stage #2: With ammonia In tetrahydrofuran at 0 - 20℃; for 3h;		90%
(S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid diisopropylethylamine salt
709031-37-8

(S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid diisopropylethylamine salt

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Stage #1: (S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid diisopropylethylamine salt With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -20 - 0℃; for 3h;
Stage #2: With ammonium carbonate In tetrahydrofuran at 0 - 20℃;		90%
With ammonia; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran1.5 g
1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid
90104-21-5

1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Stage #1: 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -25 - -20℃; for 2h; Large scale;
Stage #2: With ammonia In tetrahydrofuran at 0 - 20℃; for 3h; Large scale;		90%
With 4-methyl-morpholine; ammonia; methanesulfonyl chloride at -15 - -8℃;359.7 g
4,5-dihydro-1H-pyrrole-1,5-dicarboxylic acid 1-(1,1-dimethylethyl) sodium salt

4,5-dihydro-1H-pyrrole-1,5-dicarboxylic acid 1-(1,1-dimethylethyl) sodium salt

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride
3945-69-5

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

A

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

B

4, 6-DIMEO-1, 3,5-triazene ether (DMT-ether)

4, 6-DIMEO-1, 3,5-triazene ether (DMT-ether)

Conditions
ConditionsYield
With sodium hydroxide; sodium dihydrogenphosphate; ammonium chloride at 20℃; for 4h; pH=6.20; Conversion of starting material;A 87%
B 12%
...Expand
(5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester
178172-26-4

(5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester

A

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

B

(R)-tert-butyl 2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate

(R)-tert-butyl 2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate

Conditions
ConditionsYield
With sodium methylate; formamide In methanol at 20℃; for 4.5h;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: dmap
2: lithium triethylborohydride / toluene / -70 - -60 °C
3: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
4: water; lithium hydroxide / ethanol
5: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
View Scheme
Multi-step reaction with 4 steps
1.1: dmap / toluene / 3 h / 25 °C / Large scale
2.1: lithium triethylborohydride / toluene; tetrahydrofuran / 0.5 h / -45 °C / Large scale
2.2: 3 h / 25 °C / Large scale
3.1: lithium hydroxide monohydrate / water; ethanol / 2 h / 25 °C / Large scale
4.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -25 - -20 °C / Large scale
4.2: 3 h / 0 - 20 °C / Large scale
View Scheme
5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester
194594-23-5

5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
2: water; lithium hydroxide / ethanol
3: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
View Scheme
(S)-ethyl N-tert-butoxycarbonylpyroglutamate
144978-35-8, 144978-12-1

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lithium triethylborohydride / toluene / -70 - -60 °C
2: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
3: water; lithium hydroxide / ethanol
4: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
View Scheme
Multi-step reaction with 3 steps
1.1: lithium triethylborohydride / toluene; tetrahydrofuran / 0.5 h / -45 °C / Large scale
1.2: 3 h / 25 °C / Large scale
2.1: lithium hydroxide monohydrate / water; ethanol / 2 h / 25 °C / Large scale
3.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -25 - -20 °C / Large scale
3.2: 3 h / 0 - 20 °C / Large scale
View Scheme
ethyl (S)-pyroglutamate
7149-65-7

ethyl (S)-pyroglutamate

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: dmap
2: lithium triethylborohydride / toluene / -70 - -60 °C
3: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine
4: water; lithium hydroxide / ethanol
5: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
View Scheme
Multi-step reaction with 4 steps
1.1: dmap / toluene / 3 h / 25 °C / Large scale
2.1: lithium triethylborohydride / toluene; tetrahydrofuran / 0.5 h / -45 °C / Large scale
2.2: 3 h / 25 °C / Large scale
3.1: lithium hydroxide monohydrate / water; ethanol / 2 h / 25 °C / Large scale
4.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -25 - -20 °C / Large scale
4.2: 3 h / 0 - 20 °C / Large scale
View Scheme
4,5-duhydro-1H-pyrrole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl) dicyclohexylamine salt
709031-41-4

4,5-duhydro-1H-pyrrole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl) dicyclohexylamine salt

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water
2: ammonium hydroxide / Inert atmosphere
View Scheme
C15H20N4O6*C12H23N

C15H20N4O6*C12H23N

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
With ammonium hydroxide Inert atmosphere;
lithium (2S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylate

lithium (2S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylate

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: ethyl acetate / 0.25 h / 8 °C / Inert atmosphere
1.2: 2 h / 8 - 12 °C / Inert atmosphere
2.1: ammonium hydroxide / 0.5 h / 0 - 20 °C
View Scheme
C13H17N3O3

C13H17N3O3

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
With ammonium hydroxide at 0 - 20℃; for 0.5h;1.75 g
(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one
108963-96-8

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: lithium triethylborohydride / tetrahydrofuran / 5 - 10 °C
1.2: 3 h / 120 °C
2.1: lithium hydroxide monohydrate / methanol; water / -5 - 30 °C
3.1: 4-methyl-morpholine; methanesulfonyl chloride; ammonia / -15 - -8 °C
View Scheme
Multi-step reaction with 3 steps
1.1: lithium triethylborohydride / toluene; tetrahydrofuran / 3 h / -70 - -60 °C / Inert atmosphere
1.2: 3.33 h / -60 - 20 °C
2.1: water; lithium hydroxide / methanol / 2 h / 0 - 20 °C
3.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 3 h / -20 - 0 °C
3.2: 0 - 20 °C
View Scheme
L-Pyroglutamic acid
98-79-3

L-Pyroglutamic acid

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / -5 - 30 °C
2.1: triethylamine / toluene / -5 - 0 °C
2.2: -5 - 30 °C
3.1: lithium triethylborohydride / tetrahydrofuran / 5 - 10 °C
3.2: 3 h / 120 °C
4.1: lithium hydroxide monohydrate / methanol; water / -5 - 30 °C
5.1: 4-methyl-morpholine; methanesulfonyl chloride; ammonia / -15 - -8 °C
View Scheme
Multi-step reaction with 5 steps
1.1: thionyl chloride / 5 h / -5 - 0 °C / Large scale
2.1: dmap / toluene / 3 h / 25 °C / Large scale
3.1: lithium triethylborohydride / toluene; tetrahydrofuran / 0.5 h / -45 °C / Large scale
3.2: 3 h / 25 °C / Large scale
4.1: lithium hydroxide monohydrate / water; ethanol / 2 h / 25 °C / Large scale
5.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -25 - -20 °C / Large scale
5.2: 3 h / 0 - 20 °C / Large scale
View Scheme
methyl (S)-pyroglutamate
4931-66-2

methyl (S)-pyroglutamate

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine / toluene / -5 - 0 °C
1.2: -5 - 30 °C
2.1: lithium triethylborohydride / tetrahydrofuran / 5 - 10 °C
2.2: 3 h / 120 °C
3.1: lithium hydroxide monohydrate / methanol; water / -5 - 30 °C
4.1: 4-methyl-morpholine; methanesulfonyl chloride; ammonia / -15 - -8 °C
View Scheme
(S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate
83548-46-3

(S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium hydroxide monohydrate / methanol; water / -5 - 30 °C
2: 4-methyl-morpholine; methanesulfonyl chloride; ammonia / -15 - -8 °C
View Scheme
Multi-step reaction with 2 steps
1.1: water; lithium hydroxide / methanol / 2 h / 0 - 20 °C
2.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 3 h / -20 - 0 °C
2.2: 0 - 20 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

tetramethylammonium trifluoromethanesulphonate
25628-09-5

tetramethylammonium trifluoromethanesulphonate

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
361440-67-7

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
With n-butyllithium; C40H54NiP2 In tetrahydrofuran; hexane at 0 - 20℃; for 16h; Reagent/catalyst; Solvent; Inert atmosphere;93%
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

diiodomethane
75-11-6

diiodomethane

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
361440-67-7

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Stage #1: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester; diiodomethane With diethylzinc In water; ethyl acetate; toluene at -10 - 0℃; for 105h; Inert atmosphere;
Stage #2: With trifluoroacetic acid In water; ethyl acetate; toluene at -10 - 16℃; for 1.66667h; Reagent/catalyst; Inert atmosphere;		70%
Stage #1: diiodomethane With copper(I) bromide; zinc In tert-butyl methyl ether at 20℃; for 0.5h; Simmons-Smith Cyclopropanation; Inert atmosphere;
Stage #2: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester In tert-butyl methyl ether at 20℃; for 4.5h; Simmons-Smith Cyclopropanation; Inert atmosphere;		68%
Stage #1: diiodomethane With diethylzinc In 1,2-dimethoxyethane; dichloromethane; toluene at -30 - -25℃; for 0.75h; Simmons-Smith Reaction;
Stage #2: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester In 1,2-dimethoxyethane; dichloromethane; toluene at 22 - 24℃;
Stage #3: With sodium hydrogencarbonate In 1,2-dimethoxyethane; dichloromethane; water; toluene at 15℃; for 1h;		55%
With diethylzinc In 1,2-dimethoxyethane; dichloromethane at -30 - 20℃; Simmons-Smith Cyclopropanation; stereoselective reaction;45%
Stage #1: diiodomethane With diethylzinc In 1,2-dimethoxyethane; dichloromethane; toluene at -30 - -20℃; for 0.75h; Large scale;
Stage #2: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester In 1,2-dimethoxyethane; dichloromethane; toluene at -25 - 24℃; Large scale;
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

[1S-(<α, 3<β, 5<α)-3-aminocarbonyl]-2-azabicyclo [3.1.0] hexane-2-carboxylic acid 1,1-dimethylethyl ester

[1S-(<α, 3<β, 5<α)-3-aminocarbonyl]-2-azabicyclo [3.1.0] hexane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Stage #1: diiodomethane With diethylzinc In 1,2-dimethoxyethane; dichloromethane; toluene at -30 - 25℃; for 0.75h; Simmons-Smith Reaction;
Stage #2: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester In 1,2-dimethoxyethane; dichloromethane; toluene at 22 - 24℃;		55%
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(13)C(2)H2I2
1217038-24-8

(13)C(2)H2I2

(1S,3S,5S)-tert-butyl 3-carbamoyl-6-[13CD2]-2-azabicyclo[3.1.0]hexane-2-carboxylate
1572922-54-3

(1S,3S,5S)-tert-butyl 3-carbamoyl-6-[13CD2]-2-azabicyclo[3.1.0]hexane-2-carboxylate

Conditions
ConditionsYield
Stage #1: (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester With diethylzinc In dichloromethane; toluene at 0℃; for 0.5h; Inert atmosphere;
Stage #2: (13)C(2)H2I2 In dichloromethane; toluene at 0 - 20℃; for 17h; Simmons-Smith Cyclopropanation; Inert atmosphere;		40%
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

<14C>methylene iodide
58401-84-6

<14C>methylene iodide

(1S,3S,5S)-tert-butyl 3-carbamoyl-6-[14C]-2-azabicyclo[3.1.0]hexane-2-carboxylate

(1S,3S,5S)-tert-butyl 3-carbamoyl-6-[14C]-2-azabicyclo[3.1.0]hexane-2-carboxylate

Conditions
ConditionsYield
With water; diethylzinc In dichloromethane; toluene; pentane at -10 - 20℃; for 21h; Simmons-Smith Cyclopropanation; Inert atmosphere;10.2%
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester
709031-43-6

3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
2.1: isopropyl alcohol / 60 °C
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
4.2: 18 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: diethylzinc / dichloromethane; toluene; 1,2-dimethoxyethane / 0.75 h / -30 - -20 °C / Large scale
1.2: -25 - 24 °C / Large scale
2.1: hydrogenchloride / water; tetrahydrofuran; ethyl acetate / 18 h / 20 °C
3.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice
3.2: 20 °C
4.1: pyridine; trifluoroacetic anhydride / 0.5 h / Cooling with ice
4.2: 7.55 h / Cooling
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(R)-N-Boc-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile
1564266-92-7

(R)-N-Boc-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
2.1: isopropyl alcohol / 60 °C
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
4.2: 18 h / 20 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

saxagliptin

saxagliptin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
2.1: isopropyl alcohol / 60 °C
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
4.2: 18 h / 20 °C
5.1: hydrogenchloride / isopropyl alcohol; water / 1.5 h / 65 °C
View Scheme
Multi-step reaction with 6 steps
1.1: diethylzinc / dichloromethane; toluene; 1,2-dimethoxyethane / 0.75 h / -30 - -20 °C / Large scale
1.2: -25 - 24 °C / Large scale
2.1: hydrogenchloride / water; tetrahydrofuran; ethyl acetate / 18 h / 20 °C
3.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice
3.2: 20 °C
4.1: pyridine; trifluoroacetic anhydride / 0.5 h / Cooling with ice
4.2: 7.55 h / Cooling
5.1: dichloromethane / methanol / 20 °C / Inert atmosphere
6.1: water; dichloromethane
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(R)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile

(R)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
2.1: isopropyl alcohol / 60 °C
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
4.2: 18 h / 20 °C
5.1: hydrogenchloride / isopropyl alcohol; water / 1.5 h / 65 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid
709031-45-8

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
2: isopropyl alcohol / 60 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate
361442-01-5

tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
2: isopropyl alcohol / 60 °C
3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
View Scheme
Multi-step reaction with 3 steps
1.1: diethylzinc / dichloromethane; toluene; 1,2-dimethoxyethane / 0.75 h / -30 - -20 °C / Large scale
1.2: -25 - 24 °C / Large scale
2.1: hydrogenchloride / water; tetrahydrofuran; ethyl acetate / 18 h / 20 °C
3.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice
3.2: 20 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(R)-N-Boc-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinamide
1528611-63-3

(R)-N-Boc-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
2: isopropyl alcohol / 60 °C
3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

tert-butyl((S)-2-((1S,3S,5S)-3-(6-[13CD2])-cyano-2-azabicyclo[3.1.0]hexan-2-yl)-1-(3,5-dihydroxyadamantan-1-yl)-2-oxoethyl)carbamate
1572922-58-7

tert-butyl((S)-2-((1S,3S,5S)-3-(6-[13CD2])-cyano-2-azabicyclo[3.1.0]hexan-2-yl)-1-(3,5-dihydroxyadamantan-1-yl)-2-oxoethyl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: diethylzinc / dichloromethane; toluene / 0.5 h / 0 °C / Inert atmosphere
1.2: 17 h / 0 - 20 °C / Inert atmosphere
2.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
3.1: hydrogenchloride / 1,4-dioxane / 1.2 h / 47 °C / Inert atmosphere
4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

C17(13)CH23(2)H2N3O3*ClH
1572922-53-2

C17(13)CH23(2)H2N3O3*ClH

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: diethylzinc / dichloromethane; toluene / 0.5 h / 0 °C / Inert atmosphere
1.2: 17 h / 0 - 20 °C / Inert atmosphere
2.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
3.1: hydrogenchloride / 1,4-dioxane / 1.2 h / 47 °C / Inert atmosphere
4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide
5.1: hydrogenchloride / water; isopropyl alcohol
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

C22(14)CH33N3O4

C22(14)CH33N3O4

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: diethylzinc; water / dichloromethane; pentane; toluene / 21 h / -10 - 20 °C / Inert atmosphere
2: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
3: hydrogenchloride / 1,4-dioxane / 1.2 h / 47 °C / Inert atmosphere
4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(1S,3S,5S)-tert-butyl 3-cyano-6-[14C]-2-azabicyclo[3.1.0]hexane-2-carboxylate

(1S,3S,5S)-tert-butyl 3-cyano-6-[14C]-2-azabicyclo[3.1.0]hexane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethylzinc; water / dichloromethane; pentane; toluene / 21 h / -10 - 20 °C / Inert atmosphere
2: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(1S,3S,5S)-6-[14C]-2-azabicyclo[3.1.0]hexane-3-carbonitrile hydrochloride

(1S,3S,5S)-6-[14C]-2-azabicyclo[3.1.0]hexane-3-carbonitrile hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diethylzinc; water / dichloromethane; pentane; toluene / 21 h / -10 - 20 °C / Inert atmosphere
2: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
3: hydrogenchloride / 1,4-dioxane / 1.2 h / 47 °C / Inert atmosphere
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

6-[14C]-saxagliptin

6-[14C]-saxagliptin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: diethylzinc; water / dichloromethane; pentane; toluene / 21 h / -10 - 20 °C / Inert atmosphere
2.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
3.1: hydrogenchloride / 1,4-dioxane / 1.2 h / 47 °C / Inert atmosphere
4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide
5.1: hydrogenchloride / water; isopropyl alcohol
5.2: 10 - 20 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(1S,3S,5S)-tert-butyl 3-cyano-6-[13CD2]-2-azabicyclo[3.1.0]hexane-2-carboxylate
1572922-55-4

(1S,3S,5S)-tert-butyl 3-cyano-6-[13CD2]-2-azabicyclo[3.1.0]hexane-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: diethylzinc / dichloromethane; toluene / 0.5 h / 0 °C / Inert atmosphere
1.2: 17 h / 0 - 20 °C / Inert atmosphere
2.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
View Scheme
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
709031-38-9

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(1S,3S,5S)-6-[13CD2]-2-azabicyclo[3.1.0]hexane-3-carbonitrile hydrochloride
1572922-56-5

(1S,3S,5S)-6-[13CD2]-2-azabicyclo[3.1.0]hexane-3-carbonitrile hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: diethylzinc / dichloromethane; toluene / 0.5 h / 0 °C / Inert atmosphere
1.2: 17 h / 0 - 20 °C / Inert atmosphere
2.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 1.2 h / 0 °C
3.1: hydrogenchloride / 1,4-dioxane / 1.2 h / 47 °C / Inert atmosphere
View Scheme

tert-Butyl (2S)-2-carbamoyl-2,3-dihydropyrrole-1-carboxylate Specification

The 1H-Pyrrole-1-carboxylic acid, 2-(aminocarbonyl)-2,3-dihydro-,1,1-dimethylethyl ester, (2S)-, with the CAS registry number 709031-38-9, is also known as 2-Methyl-2-propanyl (2S)-2-carbamoyl-2,3-dihydro-1H-pyrrole-1-carboxylate. This chemical's molecular formula is C10H16N2O3 and molecular weight is 212.25. What's more, its IUPAC name is called tert-Butyl (2S)-2-carbamoyl-2,3-dihydropyrrole-1-carboxylate.

Physical properties about 1H-Pyrrole-1-carboxylic acid, 2-(aminocarbonyl)-2,3-dihydro-,1,1-dimethylethyl ester, (2S)- are: (1)ACD/LogP: -0.463; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.46; (4)ACD/LogD (pH 7.4): -0.46; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 13.34 ; (8)ACD/KOC (pH 7.4): 13.34; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 72.63 Å2; (13)Index of Refraction: 1.523; (14)Molar Refractivity: 54.54 cm3; (15)Molar Volume: 178.674 cm3; (16) Polarizability: 21.621×10-24cm3; (17)Surface Tension: 47.702 dyne/cm; (18)Density: 1.188 g/cm3; (19)Flash Point: 187.525 °C; (20)Enthalpy of Vaporization: 63.54 kJ/mol; (21)Boiling Point: 386.461 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(OC(C)(C)C)N1\C=C/C[C@H]1C(=O)N
(2) InChI: InChI=1S/C10H16N2O3/c1-10(2,3)15-9(14)12-6-4-5-7(12)8(11)13/h4,6-7H,5H2,1-3H3,(H2,11,13)/t7-/m0/s1
(3) InChIKey: ZDKSDALJIXEHOP-ZETCQYMHSA-N

Related Products

Hot Products

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View