Product Name

  • Name

    (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

  • EINECS 1308068-626-2
  • CAS No. 361440-67-7
  • Article Data10
  • CAS DataBase
  • Density 1.228 g/cm3
  • Solubility
  • Melting Point
  • Formula C11H18N2O3
  • Boiling Point 388.9 °C at 760 mmHg
  • Molecular Weight 226.276
  • Flash Point 189.024 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 361440-67-7 ((1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester)
  • Hazard Symbols
  • Synonyms Saxagliptin Intermediate; 2-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 3-(aminocarbonyl)-, 1,1-dimethylethyl ester, (1S,3S,5S)-; (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester; (1S,3S,5S)-3-aminocarbonyl-2-azabicyclo[3.1.0]hexane-2-carboxylic acid, 1,1-dimethylethyl ester; (1S,3S,5S)-3-(Amino carbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester; (1S,3S,5S)-tert-Butyl 3-carbamoyl-2-azabicyclo[3.1.0]hexane-2-carboxylate; (1s,3s,5s)-3-(aminocarbonyl)-2-azabicyclo(3.1.0)hexane-2-carboxylic acid tert-butyl
  • PSA 72.63000
  • LogP 1.50780

Synthetic route

(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%
(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid
197142-36-2

(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

[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: (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -15℃; for 0.5h;
Stage #2: With ammonia In tetrahydrofuran; 1,4-dioxane at -30 - 20℃;		84%
Stage #1: (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -15℃; for 0.583333h;
Stage #2: With ammonia In tetrahydrofuran; 1,4-dioxane at -30 - 20℃;		84%
Stage #1: (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid With C17H28N2O5; isobutyl chloroformate In tetrahydrofuran at -15℃; for 0.583333h; Inert atmosphere;
Stage #2: With ammonia In tetrahydrofuran; 1,4-dioxane at -30 - 20℃; Inert atmosphere;		84%
Stage #1: (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -20℃; for 0.5h; Inert atmosphere;
Stage #2: With ammonia In tetrahydrofuran at -5 - 20℃; for 3h;		9.84 g
(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;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

[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
Multi-step reaction with 6 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
6: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: dmap / dichloromethane / 6 h / 20 °C
2.1: lithium triethylborohydride / tetrahydrofuran; toluene / 3 h / -78 °C
2.2: -78 °C
2.3: 2 h / -78 - 20 °C
3.1: diethylzinc / 1,2-dichloro-ethane / 19 h / -15 °C
4.1: lithium hydroxide; water / methanol / 20 h / 20 - 50 °C
5.1: C17H28N2O5; isobutyl chloroformate / tetrahydrofuran / 0.58 h / -15 °C / Inert atmosphere
5.2: -30 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 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
5.1: diethylzinc / dichloromethane; toluene; 1,2-dimethoxyethane / 0.75 h / -30 - -20 °C / Large scale
5.2: -25 - 24 °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

[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
Multi-step reaction with 4 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
4: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride / toluene / 3 h / 15 - 80 °C
2.1: copper(I) bromide; trifluoroacetic acid; zinc / tetrahydrofuran / 18 h / 25 - 50 °C / Inert atmosphere
3.1: lithium hydroxide / ethanol; water / 6 h / 35 °C
4.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
4.2: 3 h / -5 - 20 °C
View Scheme
(S)-ethyl N-tert-butoxycarbonylpyroglutamate
144978-35-8, 144978-12-1

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

[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
Multi-step reaction with 5 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
5: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: lithium triethylborohydride / tetrahydrofuran; toluene / 3 h / -78 °C
1.2: -78 °C
1.3: 2 h / -78 - 20 °C
2.1: diethylzinc / 1,2-dichloro-ethane / 19 h / -15 °C
3.1: lithium hydroxide; water / methanol / 20 h / 20 - 50 °C
4.1: C17H28N2O5; isobutyl chloroformate / tetrahydrofuran / 0.58 h / -15 °C / Inert atmosphere
4.2: -30 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 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
4.1: diethylzinc / dichloromethane; toluene; 1,2-dimethoxyethane / 0.75 h / -30 - -20 °C / Large scale
4.2: -25 - 24 °C / Large scale
View Scheme
ethyl (S)-pyroglutamate
7149-65-7

ethyl (S)-pyroglutamate

[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
Multi-step reaction with 6 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
6: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: dmap / dichloromethane / 6 h / 20 °C
2.1: lithium triethylborohydride / tetrahydrofuran; toluene / 3 h / -78 °C
2.2: -78 °C
2.3: 2 h / -78 - 20 °C
3.1: diethylzinc / 1,2-dichloro-ethane / 19 h / -15 °C
4.1: lithium hydroxide; water / methanol / 20 h / 20 - 50 °C
5.1: C17H28N2O5; isobutyl chloroformate / tetrahydrofuran / 0.58 h / -15 °C / Inert atmosphere
5.2: -30 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 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
5.1: diethylzinc / dichloromethane; toluene; 1,2-dimethoxyethane / 0.75 h / -30 - -20 °C / Large scale
5.2: -25 - 24 °C / Large scale
View Scheme
(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

[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
Multi-step reaction with 3 steps
1: water; lithium hydroxide / ethanol
2: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
3: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: isopropyl alcohol / 3 h / 50 °C / Inert atmosphere
2.1: ethyl acetate / 0.25 h / 8 °C / Inert atmosphere
2.2: 2 h / 8 - 12 °C / Inert atmosphere
3.1: ammonium hydroxide / 0.5 h / 0 - 20 °C
4.1: diethylzinc / ethyl acetate; water; toluene / 105 h / -10 - 0 °C / Inert atmosphere
4.2: 1.67 h / -10 - 16 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide
2.1: sodium hydroxide / water
3.1: ammonium hydroxide / Inert atmosphere
4.1: diethylzinc / ethyl acetate; water; toluene / 105 h / -10 - 0 °C / Inert atmosphere
4.2: 1.67 h / -10 - 16 °C / Inert atmosphere
View Scheme
(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

[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
Multi-step reaction with 2 steps
1: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran
2: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C
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

[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
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water
2.1: ammonium hydroxide / Inert atmosphere
3.1: diethylzinc / ethyl acetate; water; toluene / 105 h / -10 - 0 °C / Inert atmosphere
3.2: 1.67 h / -10 - 16 °C / Inert atmosphere
View Scheme
C15H20N4O6*C12H23N

C15H20N4O6*C12H23N

[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
Multi-step reaction with 2 steps
1.1: ammonium hydroxide / Inert atmosphere
2.1: diethylzinc / ethyl acetate; water; toluene / 105 h / -10 - 0 °C / Inert atmosphere
2.2: 1.67 h / -10 - 16 °C / Inert atmosphere
View Scheme
lithium (2S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylate

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

[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
Multi-step reaction with 3 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
3.1: diethylzinc / ethyl acetate; water; toluene / 105 h / -10 - 0 °C / Inert atmosphere
3.2: 1.67 h / -10 - 16 °C / Inert atmosphere
View Scheme
(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one
108963-96-8

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

[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
Multi-step reaction with 4 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
4.1: zinc; copper(I) bromide / tert-butyl methyl ether / 0.5 h / 20 °C / Inert atmosphere
4.2: 4.5 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 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
4.1: n-butyllithium; C40H54NiP2 / tetrahydrofuran; hexane / 16 h / 0 - 20 °C / Inert atmosphere
View Scheme
L-Pyroglutamic acid
98-79-3

L-Pyroglutamic acid

[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
Multi-step reaction with 6 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
6.1: zinc; copper(I) bromide / tert-butyl methyl ether / 0.5 h / 20 °C / Inert atmosphere
6.2: 4.5 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 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
6.1: diethylzinc / dichloromethane; toluene; 1,2-dimethoxyethane / 0.75 h / -30 - -20 °C / Large scale
6.2: -25 - 24 °C / Large scale
View Scheme
methyl (S)-pyroglutamate
4931-66-2

methyl (S)-pyroglutamate

[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
Multi-step reaction with 5 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
5.1: zinc; copper(I) bromide / tert-butyl methyl ether / 0.5 h / 20 °C / Inert atmosphere
5.2: 4.5 h / 20 °C / Inert atmosphere
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

[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
Multi-step reaction with 3 steps
1.1: lithium hydroxide monohydrate / methanol; water / -5 - 30 °C
2.1: 4-methyl-morpholine; methanesulfonyl chloride; ammonia / -15 - -8 °C
3.1: zinc; copper(I) bromide / tert-butyl methyl ether / 0.5 h / 20 °C / Inert atmosphere
3.2: 4.5 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 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
3.1: n-butyllithium; C40H54NiP2 / tetrahydrofuran; hexane / 16 h / 0 - 20 °C / Inert atmosphere
View Scheme
(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-formic acid ethyl ester
214193-11-0

(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-formic acid ethyl ester

[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
Multi-step reaction with 2 steps
1.1: lithium hydroxide; water / methanol / 20 h / 20 - 50 °C
2.1: C17H28N2O5; isobutyl chloroformate / tetrahydrofuran / 0.58 h / -15 °C / Inert atmosphere
2.2: -30 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: lithium hydroxide / ethanol; water / 6 h / 35 °C
2.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
2.2: 3 h / -5 - 20 °C
View Scheme
tert-butyl (2S)-(1-tert-butoxycarbonyl)-5-hydroxypyrrolidine-2-carboxylate
228579-90-6

tert-butyl (2S)-(1-tert-butoxycarbonyl)-5-hydroxypyrrolidine-2-carboxylate

[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
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride / toluene / 3 h / 15 - 80 °C
2.1: copper(I) bromide; trifluoroacetic acid; zinc / tetrahydrofuran / 18 h / 25 - 50 °C / Inert atmosphere
3.1: lithium hydroxide / ethanol; water / 3 h / 85 °C
4.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
4.2: 3 h / -5 - 20 °C
View Scheme
(S)-di-tert-butyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate
501096-37-3

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

[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
Multi-step reaction with 3 steps
1.1: copper(I) bromide; trifluoroacetic acid; zinc / tetrahydrofuran / 18 h / 25 - 50 °C / Inert atmosphere
2.1: lithium hydroxide / ethanol; water / 3 h / 85 °C
3.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
3.2: 3 h / -5 - 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

1,2-dibromomethane
74-95-3

1,2-dibromomethane

[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 copper(I) bromide; zinc In tetrahydrofuran at 25 - 40℃; for 28h; Inert atmosphere;0.5 g
trifluoroacetic acid
76-05-1

trifluoroacetic acid

[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

(2S,4S,5S)-4,5-methano-L-proline carboxylamide trifluoroacetate

(2S,4S,5S)-4,5-methano-L-proline carboxylamide trifluoroacetate

Conditions
ConditionsYield
In dichloromethane at 0℃; for 18h;100%
In dichloromethane at 0℃; for 18h;100%
[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

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide hydrochloride

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; ethyl acetate at 20℃; for 18h;100%
With hydrogenchloride In tetrahydrofuran; water; ethyl acetate at 20℃; for 18h;100%
[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

(2S,4S,5S)-4,5-methano-L-proline carboxylamide trifluoroacetate

(2S,4S,5S)-4,5-methano-L-proline carboxylamide trifluoroacetate

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 0℃; for 12h;100%
[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

(1S,3S,5S)-tert-butyl 3-cyano-2-azabicyclo[3.1.0]hexane-2-carboxylate
361442-57-1

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

Conditions
ConditionsYield
With pyridine; trifluoroacetic anhydride at -20 - 20℃; for 9h;100%
With trifluoroacetic anhydride In pyridine at 20℃; for 4h;93.6%
With pyridine; trifluoroacetic anhydride at -20 - 20℃; for 9h;80%
methanesulfonic acid
75-75-2

methanesulfonic acid

[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

(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
In isopropyl alcohol at 60 - 70℃; for 5h;96.7%
In isopropyl alcohol at 55 - 65℃; for 3.5h; Large scale reaction;94%
In isopropyl alcohol at 60℃;80%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

[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

C21H34N2O7
1313751-21-1

C21H34N2O7

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 5h;65%
[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

(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid
197142-36-2

(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dmap / acetonitrile / 5 h / 20 °C
2.1: sodium hydroxide / tetrahydrofuran / 16 h / 20 °C
2.2: pH 3
View Scheme
[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

C37H43N5O7
1313751-22-2

C37H43N5O7

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dmap / acetonitrile / 5 h / 20 °C
2.1: sodium hydroxide / tetrahydrofuran / 16 h / 20 °C
2.2: pH 3
3.1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane / 16 h / 20 °C
View Scheme
[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

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 3 steps
1.1: isopropyl alcohol / 60 °C
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
3.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
3.2: 18 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogenchloride / water; tetrahydrofuran; ethyl acetate / 18 h / 20 °C
2.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice
2.2: 20 °C
3.1: pyridine; trifluoroacetic anhydride / 0.5 h / Cooling with ice
3.2: 7.55 h / Cooling
View Scheme
[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

(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 3 steps
1.1: isopropyl alcohol / 60 °C
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
3.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
3.2: 18 h / 20 °C
View Scheme
[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

saxagliptin

saxagliptin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: isopropyl alcohol / 60 °C
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
3.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
3.2: 18 h / 20 °C
4.1: hydrogenchloride / isopropyl alcohol; water / 1.5 h / 65 °C
View Scheme
Multi-step reaction with 5 steps
1.1: hydrogenchloride / water; tetrahydrofuran; ethyl acetate / 18 h / 20 °C
2.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice
2.2: 20 °C
3.1: pyridine; trifluoroacetic anhydride / 0.5 h / Cooling with ice
3.2: 7.55 h / Cooling
4.1: dichloromethane / methanol / 20 °C / Inert atmosphere
5.1: water; dichloromethane
View Scheme
[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

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

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: isopropyl alcohol / 60 °C
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
3.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C
3.2: 18 h / 20 °C
4.1: hydrogenchloride / isopropyl alcohol; water / 1.5 h / 65 °C
View Scheme
[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

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 2 steps
1: isopropyl alcohol / 60 °C
2: 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 2 steps
1: dichloromethane / 18 h / 0 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: hydrogenchloride / water; tetrahydrofuran; ethyl acetate / 18 h / 20 °C
2.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice
2.2: 20 °C
View Scheme
[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

(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 2 steps
1: isopropyl alcohol / 60 °C
2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h
View Scheme
[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

(1S,3S,5S)-2-[(2S)-2-triphenylmethylamino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carboxamide

(1S,3S,5S)-2-[(2S)-2-triphenylmethylamino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: isopropyl alcohol / 5 h / 60 - 70 °C
2.1: dichloromethane / 0.25 h / 25 - 35 °C
2.2: 13.25 h / 5 - 35 °C
View Scheme
Multi-step reaction with 2 steps
1: isopropyl alcohol / 5 h / 60 - 70 °C
2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 12 h / 5 - 35 °C
View Scheme
[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

(1S,3S,5S)-2-[(2S)-2-tritylamino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

(1S,3S,5S)-2-[(2S)-2-tritylamino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: isopropyl alcohol / 5 h / 60 - 70 °C
2.1: dichloromethane / 0.25 h / 25 - 35 °C
2.2: 13.25 h / 5 - 35 °C
3.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 3.5 h / 0 - 10 °C
3.2: 3.5 h / 25 °C / pH 10 - 11
View Scheme
Multi-step reaction with 3 steps
1.1: isopropyl alcohol / 5 h / 60 - 70 °C
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 12 h / 5 - 35 °C
3.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 3.5 h / 0 - 10 °C
3.2: 3.5 h / 25 °C / pH 10 - 11
View Scheme
[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

Saxagliptin hydrochloride
709031-78-7

Saxagliptin hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: isopropyl alcohol / 5 h / 60 - 70 °C
2.1: dichloromethane / 0.25 h / 25 - 35 °C
2.2: 13.25 h / 5 - 35 °C
3.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 3.5 h / 0 - 10 °C
3.2: 3.5 h / 25 °C / pH 10 - 11
4.1: water; hydrogenchloride / methanol / 3 h / 25 °C
View Scheme
Multi-step reaction with 4 steps
1.1: isopropyl alcohol / 5 h / 60 - 70 °C
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 12 h / 5 - 35 °C
3.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 3.5 h / 0 - 10 °C
3.2: 3.5 h / 25 °C / pH 10 - 11
4.1: water; hydrogenchloride / methanol / 3 h / 25 °C
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogenchloride / water; tetrahydrofuran; ethyl acetate / 18 h / 20 °C
2.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice
2.2: 20 °C
3.1: pyridine; trifluoroacetic anhydride / 0.5 h / Cooling with ice
3.2: 7.55 h / Cooling
4.1: dichloromethane / methanol / 20 °C / Inert atmosphere
View Scheme
[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

(1S,3S,5S)-2-(2-(((2r,3aR,5S,6aS)-5-hy droxy-2-methyloctahydropentalen-2-yl )amino)acetyl)-2-azabicyclo[3.1.0]hex ane-3-carbonitrile

(1S,3S,5S)-2-(2-(((2r,3aR,5S,6aS)-5-hy droxy-2-methyloctahydropentalen-2-yl )amino)acetyl)-2-azabicyclo[3.1.0]hex ane-3-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: trifluoroacetic anhydride / pyridine / 4 h / 20 °C
2.1: acetonitrile / 48 h / 20 °C
3.1: triethylamine / 4 h / 0 - 5 °C
3.2: 2 h / 0 °C
4.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 20 °C
View Scheme

(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester Specification

With the CAS registry number 361440-67-7, The IUPAC name of (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester is tert-Butyl (1R,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hexane-2-carboxylate. In addition, the formula is C11H18N2O3 and the molecular weight is 226.2722.

Physical properties about (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester are: (1)ACD/LogP: -0.534; (2)ACD/LogD (pH 5.5): -0.53; (3)ACD/LogD (pH 7.4): -0.53; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 12.20; (7)ACD/KOC (pH 7.4): 12.20; (8)#H bond acceptors: 5; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.538; (12)Molar Refractivity: 57.6 cm3; (13)Molar Volume: 184.139 cm3; (14)Polarizability: 22.834 10-24cm3; (15)Surface Tension: 49.5180015563965 dyne/cm; (16)Density: 1.229 g/cm3; (17)Flash Point: 189.024 °C; (18) Enthalpy of Vaporization: 63.821 kJ/mol; (19)Boiling Point: 388.94 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)SMILES: CC(C)(C)OC(=O)N1[C@H]2C[C@H]2C[C@H]1C(=O)N
(2)InChI: InChI=1/C11H18N2O3/c1-11(2,3)16-10(15)13-7-4-6(7)5-8(13)9(12)14/h6-8H,4-5H2,1-3H3,(H2,12,14)/t6-,7-,8-/m0/s1
(3)InChIKey: VLAGXRRGXCNITB-FXQIFTODBM

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