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Cas Database |
| 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 | Density | 1.228 g/cm3 |
| PSA | 72.63000 | LogP | 1.50780 |
| Solubility | N/A | Melting Point |
N/A |
| Formula | C11H18N2O3 | Boiling Point | 388.9 °C at 760 mmHg |
| Molecular Weight | 226.276 | Flash Point | 189.024 °C |
| Transport Information | N/A | Appearance | N/A |
| Safety | Risk Codes | N/A | |
| Molecular Structure |
|
Hazard Symbols | N/A |
| 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 |
Article Data | 10 |
(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester Synthetic route
- 709031-38-9
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
- 25628-09-5
tetramethylammonium trifluoromethanesulphonate
- 361440-67-7
[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
| Conditions | Yield |
|---|---|
| With n-butyllithium; C40H54NiP2 In tetrahydrofuran; hexane at 0 - 20℃; for 16h; Reagent/catalyst; Solvent; Inert atmosphere; | 93% |
- 197142-36-2
(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid
- 361440-67-7
[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
| Conditions | Yield |
|---|---|
| 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 |
- 709031-38-9
(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester
- 75-11-6
diiodomethane
- 361440-67-7
[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
| Conditions | Yield |
|---|---|
| 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; |
- 24424-99-5
di-tert-butyl dicarbonate
- 361440-67-7
[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
| Conditions | Yield |
|---|---|
| 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 |
- 194594-23-5
5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester
- 361440-67-7
[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
| Conditions | Yield |
|---|---|
| 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 |
- 144978-35-8, 144978-12-1
(S)-ethyl N-tert-butoxycarbonylpyroglutamate
- 361440-67-7
[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
| Conditions | Yield |
|---|---|
| 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 |
- 7149-65-7
ethyl (S)-pyroglutamate
- 361440-67-7
[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
| Conditions | Yield |
|---|---|
| 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 |
- 178172-26-4
(5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester
- 361440-67-7
[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
| Conditions | Yield |
|---|---|
| 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 |
- 709031-37-8
(S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid diisopropylethylamine salt
- 361440-67-7
[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
| Conditions | Yield |
|---|---|
| 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 |
- 709031-41-4
4,5-duhydro-1H-pyrrole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl) dicyclohexylamine salt
- 361440-67-7
[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester
| Conditions | Yield |
|---|---|
| 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 |
(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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