The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi
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inquiry1. Product advantages High purity, all above 98.5%, no impurities after dissolution We will test each batch to ensure quality OEM and private brand services designed for free Various cap colors available We can also provide MT1 peptide powd
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inquiryHenan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod
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inquiryCompany Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments
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inquirySuperior quality, moderate price & quick delivery. Appearance:White crystalloid powder Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:10g/bag,or as your request Application:For medicine , pesticide interm
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inquiryOur company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung, LG, Merck, Thermo Fisher Scientific and so o
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inquiryZhenyu biotech exported this product to many countries and regions at best price. if you are looking for the material's manufacturer or supplier in china, zhenyu biotech is your best choice. pls contact with us freely for getting detailed
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inquiryLower price, sample is available,SDS test documents are available,large stock in warehouseAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:Fine chemical intermediates, used as the main raw material for the synthe
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inquiryJinhua huayi chemical co., ltd. is dedicated to the development, production and marketing of chemicals. On the basis of equality and mutual benefit, and under the principle of customer first, credit first, quality first, we are ready to join hands
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inquiryAnsciep Chemical is a professional enterprise manufacturing and distributing fine chemicals and speciality chemicals. We have been dedicated to heterocycle compounds and phenyl rings for tens of years. This is our mature product for export. Our quali
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inquiryN-[(1S)-2-[(1S,3S,5S)-3-Cyano-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-2-oxoethyl]carbamic acid 1,1-dimethylethyl esterAppearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum
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inquiry709031-43-6 Application:intermediate
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inquiryBest Seller, High Quality, Competitive Price, Fast Delivery, Quick ResponseAppearance:powder, or liquid Storage:Stored in room temperature, ventilated place Package:Bottle, barrel, cargo, container, etc. Application:Pharmaceuticals, intermediates, AP
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United Scientific Company Located in Shanghai of China , is a competitive player in the global specialty and fine chemical market. Fenghua has both the expertise and flexibility to produce a wide range of chemicals. Focusing on developing the innovat
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inquiryplease contact us to confirm the required quantity and quote, we will provide you with COA,NMR,HPLC and other relevant informationAppearance:White powder Storage:Store in a cool place. Keep container tightly closed in a dry and well-ventilated place
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inquiryAppearance:white powder Storage:store in cool place. Keep container tightly closed in a dry and well-ventilated place. Package:aluminium foil bag; drum; as per your customers' requests Application:pharmaceutical Intermediate
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inquiryAppearance:White crystalloid powder Storage:room temperature Package:25kg/Fiber Can Transportation:By air Port:Tianjin
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inquiryhigh purity Application:Drug intermediates Materials intermediates and active molecules
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inquiry3-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 | Yield |
---|---|
Stage #1: Na(1+)*C17H26NO5(1-) With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In ethyl acetate; acetonitrile at 20℃; for 5h; Stage #2: (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile In ethyl acetate; acetonitrile at 20℃; for 2h; Reagent/catalyst; | 97.9% |
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
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 | Yield |
---|---|
Stage #1: 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 With pyridine; trifluoroacetic anhydride In tetrahydrofuran for 1h; Stage #2: With potassium hydroxide In methanol at 20℃; for 18h; | 92% |
Stage #1: 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 With triethylamine In ethyl acetate at 5 - 25℃; for 0.666667h; Stage #2: With trifluoroacetic anhydride In ethyl acetate at 20℃; for 2h; | 92.3% |
Stage #1: 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 With pyridine; trifluoroacetic anhydride In tetrahydrofuran at 0℃; for 1.5h; Stage #2: With potassium carbonate In tetrahydrofuran; methanol at 20 - 25℃; pH=> 10; | 89% |
(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile 4-methylbenzenesulfonate
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 | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 2h; | 77% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
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 | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 2.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h 2.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 17.5 h / 0 °C / Inert atmosphere 2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C 2.2: 20 - 25 °C / pH > 10 View Scheme | |
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h 2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 18 h / 20 °C View Scheme |
(S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile
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 | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 78 percent / aq. HCl; AcOH / 18 h / 80 °C 2.1: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 3.1: 4.07 g / K2CO3 / dimethylformamide / 19 h 4.1: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C 5.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 6.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h 6.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: hydrogenchloride; water / acetic acid / 80 °C 2.1: hydrogen; palladium 10% on activated carbon / acetic acid 3.1: triethylamine / methanol 4.1: potassium permanganate; potassium hydroxide / 90 °C 5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h 6.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C 6.2: 18 h / 20 °C View Scheme |
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 | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 2.1: 4.07 g / K2CO3 / dimethylformamide / 19 h 3.1: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C 4.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 5.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h 5.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: hydrogen; palladium 10% on activated carbon / acetic acid 2.1: triethylamine / methanol 3.1: potassium permanganate; potassium hydroxide / 90 °C 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h 5.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C 5.2: 18 h / 20 °C View Scheme |
1-adamantanemethanol
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 | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C 2.1: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating 3.1: 78 percent / aq. HCl; AcOH / 18 h / 80 °C 4.1: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 5.1: 4.07 g / K2CO3 / dimethylformamide / 19 h 6.1: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C 7.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 8.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h 8.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C View Scheme |
1-Adamantanecarboxylic acid
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 | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: 100 percent / diethyl ether; hexane; methanol / 3 h / 20 °C 2.1: 96 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C 3.1: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C 4.1: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating 5.1: 78 percent / aq. HCl; AcOH / 18 h / 80 °C 6.1: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 7.1: 4.07 g / K2CO3 / dimethylformamide / 19 h 8.1: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C 9.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 10.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h 10.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: sulfuric acid; nitric acid; water / -5 - 1 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 2.5 h / 0 - 31 °C 2.2: 14.5 h / 0 - 30 °C 2.3: 1 h / 0 - 10 °C 3.1: potassium bromide; sodium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane; water / 0 - 5 °C 4.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C 5.1: water / 0.17 h / 0 - 2 °C 5.2: 14.5 h / -4 - 80 °C 6.1: hydrogenchloride; water / 1 h / 24 - 80 °C 6.2: 12 h / 80 - 82 °C 7.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 8.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 8.2: 2.08 h / 3 - 26 °C 8.3: 12 h / 40 °C 9.1: benzotriazol-1-ol / dichloromethane / 0.08 h / -5 - 0 °C 9.2: 15.5 h / -7 - 10 °C 10.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 6.33 h / -3 - 15 °C 10.2: 7 - 15 °C / pH 10 - 10.5 View Scheme |
1-Adamantanecarbaldehyde
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 | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating 2.1: 78 percent / aq. HCl; AcOH / 18 h / 80 °C 3.1: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 4.1: 4.07 g / K2CO3 / dimethylformamide / 19 h 5.1: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C 6.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 7.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h 7.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: sodium hydrogensulfite / 0 - 60 °C 2.1: hydrogenchloride; water / acetic acid / 80 °C 3.1: hydrogen; palladium 10% on activated carbon / acetic acid 4.1: triethylamine / methanol 5.1: potassium permanganate; potassium hydroxide / 90 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h 7.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C 7.2: 18 h / 20 °C View Scheme |
methyl adamantane-1-carboxylate
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 | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: 96 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C 2.1: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C 3.1: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating 4.1: 78 percent / aq. HCl; AcOH / 18 h / 80 °C 5.1: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 6.1: 4.07 g / K2CO3 / dimethylformamide / 19 h 7.1: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C 8.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 9.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h 9.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C View Scheme |
(S)-(+)-β-amino-1-adamantaneacetic acid
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 | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 4.07 g / K2CO3 / dimethylformamide / 19 h 2.1: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C 3.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 4.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h 4.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C View Scheme |
(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid
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 | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C 2.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 3.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h 3.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium permanganate; potassium hydroxide / 90 °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 2 steps 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 / 20.5 h / 0 - 20 °C / Inert atmosphere 2: pyridine; potassium bromate; rhodium(III) chloride hydrate / water; acetonitrile / 60 °C View Scheme |
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 | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: ethyl acetate / 17.42 h / 20 - 70 °C / Resolution of racemate 2.1: hydrogenchloride / ethyl acetate; water / pH 3 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 17.5 h / 0 °C / Inert atmosphere 4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C 4.2: 20 - 25 °C / pH > 10 View Scheme |
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 | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride / ethyl acetate; water / pH 3 2.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 17.5 h / 0 °C / Inert atmosphere 3.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C 3.2: 20 - 25 °C / pH > 10 View Scheme |
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 | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 17.5 h / 0 °C / Inert atmosphere 2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C 2.2: 20 - 25 °C / pH > 10 View Scheme | |
Multi-step reaction with 2 steps 1.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice 1.2: 20 °C 2.1: pyridine; trifluoroacetic anhydride / 0.5 h / Cooling with ice 2.2: 7.55 h / Cooling View Scheme |
N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine
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 | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine; isobutyl chloroformate / tetrahydrofuran / 1.5 h / -8 °C 1.2: 18 h / -8 - 25 °C 2.1: ethyl acetate / 17.42 h / 20 - 70 °C / Resolution of racemate 3.1: hydrogenchloride / ethyl acetate; water / pH 3 4.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 17.5 h / 0 °C / Inert atmosphere 5.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C 5.2: 20 - 25 °C / pH > 10 View Scheme |
(S)-(+)-(adamant-1-yl)aminoacetic acid hydrochloride
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 | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: triethylamine / methanol 2.1: potassium permanganate; potassium hydroxide / 90 °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 |
5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl 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
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine 2.1: water; lithium hydroxide / ethanol 3.1: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 4.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C 5.1: isopropyl alcohol / 60 °C 6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h 7.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C 7.2: 18 h / 20 °C View Scheme |
(S)-ethyl N-tert-butoxycarbonylpyroglutamate
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 | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: lithium triethylborohydride / toluene / -70 - -60 °C 2.1: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine 3.1: water; lithium hydroxide / ethanol 4.1: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 5.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C 6.1: isopropyl alcohol / 60 °C 7.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h 8.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C 8.2: 18 h / 20 °C View Scheme | |
Multi-step reaction with 7 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 5.1: hydrogenchloride / water; tetrahydrofuran; ethyl acetate / 18 h / 20 °C 6.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice 6.2: 20 °C 7.1: pyridine; trifluoroacetic anhydride / 0.5 h / Cooling with ice 7.2: 7.55 h / Cooling View Scheme |
ethyl (S)-pyroglutamate
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 | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: dmap 2.1: lithium triethylborohydride / toluene / -70 - -60 °C 3.1: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine 4.1: water; lithium hydroxide / ethanol 5.1: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 6.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C 7.1: isopropyl alcohol / 60 °C 8.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h 9.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C 9.2: 18 h / 20 °C View Scheme | |
Multi-step reaction with 8 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 6.1: hydrogenchloride / water; tetrahydrofuran; ethyl acetate / 18 h / 20 °C 7.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice 7.2: 20 °C 8.1: pyridine; trifluoroacetic anhydride / 0.5 h / Cooling with ice 8.2: 7.55 h / Cooling View Scheme |
(5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl 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
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: water; lithium hydroxide / ethanol 2.1: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 3.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C 4.1: isopropyl alcohol / 60 °C 5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h 6.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C 6.2: 18 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: lithium hydroxide monohydrate / water; ethanol / 2 h / 25 °C / Large scale 2.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -25 - -20 °C / Large scale 2.2: 3 h / 0 - 20 °C / Large scale 3.1: diethylzinc / dichloromethane; toluene; 1,2-dimethoxyethane / 0.75 h / -30 - -20 °C / Large scale 3.2: -25 - 24 °C / Large scale 4.1: hydrogenchloride / water; tetrahydrofuran; ethyl acetate / 18 h / 20 °C 5.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Cooling with acetone-dry ice 5.2: 20 °C 6.1: pyridine; trifluoroacetic anhydride / 0.5 h / Cooling with ice 6.2: 7.55 h / Cooling View Scheme |
(S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid diisopropylethylamine salt
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 | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 2.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C 3.1: isopropyl alcohol / 60 °C 4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h 5.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C 5.2: 18 h / 20 °C View Scheme |
(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
Conditions | Yield |
---|---|
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 |
[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
Conditions | Yield |
---|---|
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,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid
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 | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h 2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 18 h / 20 °C View Scheme |
C25H32F3N3O5
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 | Yield |
---|---|
With potassium carbonate In methanol; water at 40 - 45℃; for 3h; | 100 g |
[(S)-1-Adamantan-1-yl-2-((1S,3S,5S)-3-cyano-2-aza-bicyclo[3.1.0]hex-2-yl)-2-oxo-ethyl]-carbamic acid tert-butyl 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
Conditions | Yield |
---|---|
With pyridine; potassium bromate; rhodium(III) chloride hydrate In water; acetonitrile at 60℃; Solvent; |
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 | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C 2.1: water / 0.17 h / 0 - 2 °C 2.2: 14.5 h / -4 - 80 °C 3.1: hydrogenchloride; water / 1 h / 24 - 80 °C 3.2: 12 h / 80 - 82 °C 4.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 5.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 5.2: 2.08 h / 3 - 26 °C 5.3: 12 h / 40 °C 6.1: benzotriazol-1-ol / dichloromethane / 0.08 h / -5 - 0 °C 6.2: 15.5 h / -7 - 10 °C 7.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 6.33 h / -3 - 15 °C 7.2: 7 - 15 °C / pH 10 - 10.5 View Scheme |
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 | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: water / 0.17 h / 0 - 2 °C 1.2: 14.5 h / -4 - 80 °C 2.1: hydrogenchloride; water / 1 h / 24 - 80 °C 2.2: 12 h / 80 - 82 °C 3.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 4.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 4.2: 2.08 h / 3 - 26 °C 4.3: 12 h / 40 °C 5.1: benzotriazol-1-ol / dichloromethane / 0.08 h / -5 - 0 °C 5.2: 15.5 h / -7 - 10 °C 6.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 6.33 h / -3 - 15 °C 6.2: 7 - 15 °C / pH 10 - 10.5 View Scheme |
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 | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: hydrogenchloride; water / 1 h / 24 - 80 °C 1.2: 12 h / 80 - 82 °C 2.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 3.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 3.2: 2.08 h / 3 - 26 °C 3.3: 12 h / 40 °C 4.1: benzotriazol-1-ol / dichloromethane / 0.08 h / -5 - 0 °C 4.2: 15.5 h / -7 - 10 °C 5.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 6.33 h / -3 - 15 °C 5.2: 7 - 15 °C / pH 10 - 10.5 View Scheme |
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 | Yield |
---|---|
With hydrogenchloride In water; isopropyl alcohol at 60 - 65℃; for 2.08333h; Temperature; | 98.4% |
Stage #1: 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 With hydrogenchloride In water; isopropyl alcohol at 20 - 65℃; for 2.08333h; Stage #2: With sodium hydroxide In dichloromethane; water; isopropyl alcohol Product distribution / selectivity; | 86% |
With hydrogenchloride In water; isopropyl alcohol at 60℃; for 2h; | 78% |
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
trifluoroacetic acid
(S)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 2.5h; | 95% |
In dichloromethane at 20℃; for 2.5h; | 90% |
In dichloromethane at -5 - 2℃; | 17.05 g |
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 | Yield |
---|---|
With hydrogenchloride In water; isopropyl alcohol at 60 - 65℃; for 3h; | 89% |
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
saxagliptin monohydrate
Conditions | Yield |
---|---|
Stage #1: 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 With hydrogenchloride In methanol; dichloromethane; water for 18h; Stage #2: With sodium hydroxide; water In methanol; dichloromethane for 0.333333h; pH=9.0 - 10.5; Product distribution / selectivity; | 81% |
Stage #1: 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 With hydrogenchloride In water; ethyl acetate at 23℃; for 4h; Stage #2: With water; potassium carbonate In ethyl acetate at 16 - 20℃; for 2h; Product distribution / selectivity; | 77% |
Stage #1: 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 With hydrogenchloride In water; isopropyl alcohol at 65℃; for 1.5h; Stage #2: With sodium hydroxide; water; potassium carbonate In dichloromethane; isopropyl alcohol pH=~ 9; Product distribution / selectivity; |
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
nicotinic acid
Conditions | Yield |
---|---|
Stage #1: 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 With hydrogenchloride; water at 30 - 65℃; Stage #2: nicotinic acid In dichloromethane at 20 - 30℃; Solvent; | 80% |
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
sodium benzoate
Conditions | Yield |
---|---|
Stage #1: 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 With hydrogenchloride In water; ethyl acetate at 20℃; Stage #2: sodium benzoate In water; isopropyl alcohol | 79% |
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
salicylic acid
Conditions | Yield |
---|---|
Stage #1: 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 With hydrogenchloride In water; isopropyl alcohol at 30 - 65℃; Stage #2: salicylic acid In dichloromethane at 20 - 30℃; | 77% |
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 | Yield |
---|---|
With hydrogenchloride In water; ethyl acetate at 20 - 25℃; for 3h; |
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
Saxagliptin hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride / isopropyl alcohol; water / 2.08 h / 20 - 65 °C 2: 20 - 30 °C 3: hydrogenchloride; water / acetone / 1.25 h View Scheme | |
With hydrogenchloride In propan-1-ol; water Product distribution / selectivity; Reflux; | |
With hydrogenchloride; water In isopropyl alcohol at 20 - 65℃; for 1h; | 50 g |
With dichloromethane In methanol at 20℃; Inert atmosphere; |
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
(1S,3S,5S)-2-[(2S)-2-propan-2-ylideneamino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]-hexane-3-carbonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / isopropyl alcohol; water / 2.08 h / 20 - 65 °C 2: 20 - 30 °C View Scheme |
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