Chengdu AstaTech Chemical Technology Co., Ltd. is a wholly-owned subsidiary of AstaTech (Chengdu) BioPharmaceutical Co., Ltd. It has overall accountability for AstaTech’s product list and sales and promotion of chemical reagents in China. The company
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inquiryOur advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva
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inquiryHenan Tianfu Chemical Co., Ltd. is located in Zhengzhou High-tech Development Zone with import and export license. We passed ISO 9001:2008 in 2009, and won "High-tech Enterprise" by provincial government in 2013.The objective of the com
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inquiryProduct Name: 2-Azabicyclo[2.2.1]hept-5-en-3-one Synonyms: 1-Azabicyclo[2.2.1]hept-5-en-3-one;(+/-)-2-Azabicyclo[2.2.1]hept-;2-AZABICYCLO(2.2.1)HEPT-5-EN-3-ONE, (VINCE LACTAM);2-Azabicyclo(2,2,1,)hept-5-en-
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inquiryProduct Name: ((1R,4S)-2-Azabicyclo[2.2.1]hept-5-en-3-one CAS: 79200-56-9 MF: C6H7NO MW: 109.13 EINECS: 418-530-1 Mol File: 79200-56-9.mol ((1R,4S)-2-Azabicyclo[2.2.1]hept-5-en-3-one Structure ((1R,4S)-2-Azabicyclo[2.2.1]hept-5-en
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inquiryProduct name: ((1R,4S)-2-Azabicyclo[2,2,1]hept-5-en-3-one CAS No.:79200-56-9 Molecule Formula:C6H7NO Molecule Weight:109.13 Purity: 99.0% Package: 25kg/drum Description:Off-white crystalline powder Manufacture Standards:Enterprise Sta
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inquiry(1R,4S)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
With methanol; ammonium hydroxide for 13h; Ambient temperature; | 51% |
With ammonium hydroxide In methanol for 12h; Ambient temperature; | 51% |
racemic 2-azabicyclo[2.2.1]hept-5-en-3-one
A
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
B
(1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid
Conditions | Yield |
---|---|
With (+)-γ-lactamase from Bradyrhizobium japonicum USDA 6 In aq. buffer at 45℃; for 1h; pH=8; Catalytic behavior; Temperature; pH-value; Resolution of racemate; Enzymatic reaction; enantioselective reaction; | A 49.9% B n/a |
With cloned (+)-γ-lactamase at 25℃; for 1h; pH=7.5; Ring cleavage; |
racemic 2-azabicyclo[2.2.1]hept-5-en-3-one
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
With A. viscous (NCIM No.2451) In phosphate buffer for 21h; pH=7.5; | 31.2% |
With Penicillium thomi AM91 for 48h; Reagent/catalyst; Enzymatic reaction; | n/a |
2-azabicyclo[2.2.1.]hept-5-en-3-one
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate In water; acetonitrile at 0℃; for 0.283333h; Yield given; |
2-azabicyclo[2.2.1.]hept-5-en-3-one
A
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
B
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one
Conditions | Yield |
---|---|
With brucine In methanol at 20℃; for 6h; | |
With Methylobacterium sp. Y1-6 at 30℃; for 24h; Overall yield = 19 %Chromat.; | A n/a B n/a |
With malonamidase E2 (MAE2) In aq. phosphate buffer at 30℃; for 24h; pH=7.5; Resolution of racemate; Enzymatic reaction; | A n/a B n/a |
With Cu-(R)-2,2'-dihydroxy-1,1'-binaphthalene-6,6'-dicarboxylic acid organic framework silica composite In ethanol; hexane Resolution of racemate; |
2-azabicyclo[2.2.1.]hept-5-en-3-one
A
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
B
(1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid
Conditions | Yield |
---|---|
With lactamase Enzymatic reaction; | |
With Bradyrhizobium japonicum USDA 6 (+)-γ-lactamase In aq. buffer at 50℃; pH=6; Enzymatic reaction; enantioselective reaction; | A n/a B n/a |
2-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 43 percent / various solvent(s) / 0.5 h / Ambient temperature; immobilized lipase PS on diatomite 2: 90 percent / H2O / diisopropyl ether / 3 h / Ambient temperature; lipase PS 3: 51 percent / aq. NH3 / methanol / 12 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 2: 51 percent / Nh4OH, MeOH / 13 h / Ambient temperature View Scheme |
N-acetoxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 41 percent / H2O / diisopropyl ether / 3 h / Ambient temperature; lipase PS 2: 51 percent / aq. NH3 / methanol / 12 h / Ambient temperature View Scheme |
(1R,4S)-N-acetoxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / H2O / diisopropyl ether / 3 h / Ambient temperature; lipase PS 2: 51 percent / aq. NH3 / methanol / 12 h / Ambient temperature View Scheme |
(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-azabicyclo<2.2.1>-3-heptanone
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 2: 97 percent / TBAF / tetrahydrofuran / 0.33 h 3: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 4: 98 percent / DBU / xylene / 16.5 h / Heating 5: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 2: 97 percent / TBAF / tetrahydrofuran / 0.33 h 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 4: 20 percent 5: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 6: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 2: 97 percent / TBAF / tetrahydrofuran / 0.33 h 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 4: 40 percent / LiHMDS 5: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 6: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
(1R,4S,6R)-6-Iodo-2-(p-methoxybenzyl)-2-azabicyclo<2.2.1>-3-heptanone
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 98 percent / DBU / xylene / 16.5 h / Heating 2: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
(1R,4S,6S)-6-Hydroxy-2-(p-methoxybenzyl)-2-azabicyclo<2.2.1>-3-heptanone
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 2: 98 percent / DBU / xylene / 16.5 h / Heating 3: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 2: 20 percent 3: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 4: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 2: 40 percent / LiHMDS 3: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 4: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
(1R,4S)-2-(p-Methoxybenzyl)-2-azabicylo<2.2.1>heptane-3,6-dione
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 20 percent 2: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 3: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1: 40 percent / LiHMDS 2: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 3: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-benzyl-2-azabicyclo<2.2.1>-3-heptanone
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 2: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 3: 97 percent / TBAF / tetrahydrofuran / 0.33 h 4: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 5: 98 percent / DBU / xylene / 16.5 h / Heating 6: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 2: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 3: 97 percent / TBAF / tetrahydrofuran / 0.33 h 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 5: 20 percent 6: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 7: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 2: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 3: 97 percent / TBAF / tetrahydrofuran / 0.33 h 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 5: 40 percent / LiHMDS 6: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 7: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
(5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 2: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 3: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 4: 97 percent / TBAF / tetrahydrofuran / 0.33 h 5: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 6: 98 percent / DBU / xylene / 16.5 h / Heating 7: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 8 steps 1: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 2: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 3: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 4: 97 percent / TBAF / tetrahydrofuran / 0.33 h 5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 6: 20 percent 7: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 8: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 8 steps 1: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 2: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 3: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 4: 97 percent / TBAF / tetrahydrofuran / 0.33 h 5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 6: 40 percent / LiHMDS 7: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 8: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
(5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-(hydroxymethyl)-2-piperidinone
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 2: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 3: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 4: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 5: 97 percent / TBAF / tetrahydrofuran / 0.33 h 6: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 7: 98 percent / DBU / xylene / 16.5 h / Heating 8: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 9 steps 1: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 2: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 3: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 4: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 5: 97 percent / TBAF / tetrahydrofuran / 0.33 h 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 7: 20 percent 8: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 9: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 9 steps 1: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 2: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 3: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 4: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 5: 97 percent / TBAF / tetrahydrofuran / 0.33 h 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 7: 40 percent / LiHMDS 8: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 9: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-(p-methoxybenzyl)-2-azabicyclo<2.2.1>-3-heptanone
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 97 percent / TBAF / tetrahydrofuran / 0.33 h 2: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 3: 98 percent / DBU / xylene / 16.5 h / Heating 4: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1: 97 percent / TBAF / tetrahydrofuran / 0.33 h 2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 3: 20 percent 4: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 5: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1: 97 percent / TBAF / tetrahydrofuran / 0.33 h 2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 3: 40 percent / LiHMDS 4: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 5: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(hydroxymethyl)-2-piperidinone
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 89 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 22 h 2: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 3: 97 percent / TBAF / tetrahydrofuran / 0.33 h 4: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 5: 98 percent / DBU / xylene / 16.5 h / Heating 6: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1: 89 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 22 h 2: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 3: 97 percent / TBAF / tetrahydrofuran / 0.33 h 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 5: 20 percent 6: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 7: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1: 89 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 22 h 2: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 3: 97 percent / TBAF / tetrahydrofuran / 0.33 h 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 5: 40 percent / LiHMDS 6: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 7: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 2: 97 percent / TBAF / tetrahydrofuran / 0.33 h 3: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 4: 98 percent / DBU / xylene / 16.5 h / Heating 5: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 2: 97 percent / TBAF / tetrahydrofuran / 0.33 h 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 4: 20 percent 5: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 6: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 2: 97 percent / TBAF / tetrahydrofuran / 0.33 h 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 4: 40 percent / LiHMDS 5: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 6: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
(5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 2: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 3: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 4: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 5: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 6: 97 percent / TBAF / tetrahydrofuran / 0.33 h 7: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 8: 98 percent / DBU / xylene / 16.5 h / Heating 9: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 10 steps 1: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 2: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 3: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 4: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 5: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 6: 97 percent / TBAF / tetrahydrofuran / 0.33 h 7: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 8: 20 percent 9: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 10: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 10 steps 1: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 2: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 3: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 4: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 5: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 6: 97 percent / TBAF / tetrahydrofuran / 0.33 h 7: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 8: 40 percent / LiHMDS 9: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 10: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
Trifluoro-methanesulfonic acid (1R,4S)-2-(4-methoxy-benzyl)-3-oxo-2-aza-bicyclo[2.2.1]hept-5-en-6-yl ester
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 2: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 2: 89 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 22 h 3: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 4: 97 percent / TBAF / tetrahydrofuran / 0.33 h 5: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 6: 98 percent / DBU / xylene / 16.5 h / Heating 7: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 8 steps 1: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 2: 89 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 22 h 3: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 4: 97 percent / TBAF / tetrahydrofuran / 0.33 h 5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 6: 20 percent 7: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 8: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 8 steps 1: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 2: 89 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 22 h 3: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 4: 97 percent / TBAF / tetrahydrofuran / 0.33 h 5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 6: 40 percent / LiHMDS 7: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 8: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: imidazole / dimethylformamide / 15 h 2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h 3: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 4: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 5: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 6: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 7: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 8: 97 percent / TBAF / tetrahydrofuran / 0.33 h 9: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 10: 98 percent / DBU / xylene / 16.5 h / Heating 11: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 12 steps 1: imidazole / dimethylformamide / 15 h 2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h 3: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 4: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 5: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 6: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 7: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 8: 97 percent / TBAF / tetrahydrofuran / 0.33 h 9: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 10: 20 percent 11: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 12: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 12 steps 1: imidazole / dimethylformamide / 15 h 2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h 3: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 4: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 5: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 6: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 7: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 8: 97 percent / TBAF / tetrahydrofuran / 0.33 h 9: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 10: 40 percent / LiHMDS 11: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 12: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
(5S,6R)-5-Hydroxy-6-<(benzyloxy)methyl>-2-piperidinone
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: 92 percent / imidazole / dimethylformamide / 15 h 2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h 3: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 4: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 5: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 6: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 7: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 8: 97 percent / TBAF / tetrahydrofuran / 0.33 h 9: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 10: 98 percent / DBU / xylene / 16.5 h / Heating 11: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 12 steps 1: 92 percent / imidazole / dimethylformamide / 15 h 2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h 3: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 4: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 5: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 6: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 7: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 8: 97 percent / TBAF / tetrahydrofuran / 0.33 h 9: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 10: 20 percent 11: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 12: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 12 steps 1: 92 percent / imidazole / dimethylformamide / 15 h 2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h 3: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 4: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 5: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 6: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 7: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 8: 97 percent / TBAF / tetrahydrofuran / 0.33 h 9: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 10: 40 percent / LiHMDS 11: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 12: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
(5S,6R)-5-<(tert-Butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h 2: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 3: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 4: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 5: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 6: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 7: 97 percent / TBAF / tetrahydrofuran / 0.33 h 8: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h 9: 98 percent / DBU / xylene / 16.5 h / Heating 10: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 11 steps 1: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h 2: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 3: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 4: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 5: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 6: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 7: 97 percent / TBAF / tetrahydrofuran / 0.33 h 8: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 9: 20 percent 10: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 11: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme | |
Multi-step reaction with 11 steps 1: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h 2: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h 3: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h 4: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min 5: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min 6: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h 7: 97 percent / TBAF / tetrahydrofuran / 0.33 h 8: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min 9: 40 percent / LiHMDS 10: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h 11: CAN / acetonitrile; H2O / 0.28 h / 0 °C View Scheme |
(–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
2-azabicyclo[2.2.1.]hept-5-en-3-one
A
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
B
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one
C
(1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid
Conditions | Yield |
---|---|
With Nocardia farcinica-polyamidase (NfpolyA) In aq. phosphate buffer at 30℃; for 24h; pH=7.5; Resolution of racemate; Enzymatic reaction; | A n/a B n/a C n/a |
2-azabicyclo[2.2.1.]hept-5-en-3-one
A
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
B
(1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid
C
(-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid
Conditions | Yield |
---|---|
With Rhodococcus globerulus-amidase (AMI) In aq. phosphate buffer at 30℃; for 24h; pH=7.5; Resolution of racemate; Enzymatic reaction; | A n/a B n/a C n/a |
racemic 2-azabicyclo[2.2.1]hept-5-en-3-one
A
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
B
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one
C
(-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid
Conditions | Yield |
---|---|
With water; lipase B from Candida antarctica In isopropyl alcohol at 60℃; for 0.5h; Enzymatic reaction; | A n/a B n/a C n/a |
di-tert-butyl dicarbonate
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran | 100% |
With dmap In tetrahydrofuran at 20℃; for 3h; | 99% |
With dmap In dichloromethane for 16h; Inert atmosphere; | 98% |
methanol
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
(–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride at 0℃; for 2h; | 100% |
With thionyl chloride at 0 - 20℃; for 14h; | 100% |
With thionyl chloride at 0℃; | 100% |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
(+)-2-Azabicyclo<2.2.1>heptan-3-one
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 5h; atmospheric pressure; | 100% |
With hydrogen; acetic acid; palladium on activated charcoal In ethyl acetate at 20℃; under 2068.59 Torr; for 1.5h; | 98% |
With palladium 10% on activated carbon; hydrogen In methanol for 3h; | 98% |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
(1S,3R)-3-aminocyclopentanecarboxylic acid
Conditions | Yield |
---|---|
With hydrogen; palladium 10% on activated carbon In ethyl acetate at 20℃; for 24h; | 100% |
With hydrogen; palladium 10% on activated carbon In ethyl acetate at 20℃; for 24h; | 100% |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
(1S,4R)-(-)ethyl-4-aminocyclopent-2-ene-1-carboxylate hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 2h; Heating / reflux; | 100% |
With thionyl chloride In ethanol at 10 - 30℃; for 1h; Solvent; Reagent/catalyst; |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
(1R,4S,5R,6S)-5,6-dihydroxy-2-azabicyclo[2.2.1]heptan-3-one
Conditions | Yield |
---|---|
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In 1,4-dioxane at 0 - 20℃; for 3h; | 98% |
With osmium(VIII) oxide; 4-methylmorpholine N-oxide; 4-methylmorpholine 4-oxide monohydrate In 1,4-dioxane; water at 0 - 20℃; for 3h; | 98% |
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; tert-butyl alcohol at 70℃; for 0.5h; | 94% |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 20 - 60℃; for 18h; Ring cleavage; | 97% |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
(-)-(1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride | 95% |
With hydrogenchloride for 1h; Heating; | |
With hydrogenchloride; water at 80℃; for 2h; |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: pent-4-enoyl chloride In tetrahydrofuran at 20℃; Inert atmosphere; | 91% |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
benzoyl chloride
Conditions | Yield |
---|---|
In pyridine | 90% |
di-tert-butyl dicarbonate
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
tert-butyl (1R,4S)-(+)-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate
Conditions | Yield |
---|---|
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 7h; Heating; Stage #2: di-tert-butyl dicarbonate at 25℃; for 14h; Further stages.; | 87% |
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 7h; Heating; Stage #2: di-tert-butyl dicarbonate at 20℃; for 14h; Further stages.; | 52% |
methanol
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 12h; Stage #2: methanol With thionyl chloride at 0 - 20℃; for 24h; | 84% |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
p-methoxybenzyl chloride
(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h; | 83% |
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 50℃; for 3h; Inert atmosphere; | 75% |
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Cooling with ice; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 3h; | 65% |
With potassium hydroxide Yield given; | |
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: p-methoxybenzyl chloride In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 25℃; for 1h; Solvent; Reagent/catalyst; Temperature; |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
4-iodo-2-methoxybenzoic acid-methyl ester
methyl 2-methoxy-4-((1R,4S)-3-oxo-2-azabicyclo[2.2.1]hept-5-en-2-yl)benzoate
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In toluene at 110℃; for 18h; Inert atmosphere; | 74% |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
4-Methoxybenzyl alcohol
(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one
Conditions | Yield |
---|---|
Stage #1: 4-Methoxybenzyl alcohol With hydrogenchloride In water for 1h; Stage #2: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 6.5h; Inert atmosphere; | 73% |
ethene
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; under 760.051 Torr; for 2.5h; | 70% |
oxirane
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With lithium diisopropyl amide In tetrahydrofuran for 1h; Stage #2: oxirane In tetrahydrofuran | 67% |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
benzyl chloroformate
Conditions | Yield |
---|---|
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 60℃; for 27h; Inert atmosphere; Stage #2: benzyl chloroformate With trimethylamine In tetrahydrofuran; water at 0 - 20℃; for 48h; | 63% |
Conditions | Yield |
---|---|
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: but-3-enoyl chloride In tetrahydrofuran at 20℃; Inert atmosphere; | 63% |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
benzenesulfonyl chloride
Conditions | Yield |
---|---|
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil at 20℃; for 1.5h; Inert atmosphere; | 62% |
diazomethane
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
palladium diacetate In diethyl ether at 20℃; for 24h; | 62% |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
isoprene
Conditions | Yield |
---|---|
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 1,3-bis-(diphenylphosphino)propane; sodium carbonate In toluene at 140℃; for 20h; Inert atmosphere; regioselective reaction; | 55% |
2-(chloromethyl)iodobenzene
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
N-(2'-iodobenzyl)-2-aza-3-oxobicyclo[2.2.1]hept-5-ene
Conditions | Yield |
---|---|
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With sodium hydride In tetrahydrofuran at 20℃; for 1h; Metallation; Stage #2: 2-(chloromethyl)iodobenzene In tetrahydrofuran for 12h; Alkylation; Heating; | 53% |
With sodium hydride In tetrahydrofuran at 65℃; for 16h; Substitution; | 53% |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
(1S,2R,4S,5R)-3-oxa-6-azatricyclo[3.2.1.02,4]octan-7-one
Conditions | Yield |
---|---|
With disodium hydrogenphosphate; sodium dihydrogenphosphate In water at 0℃; for 7h; pH=6; | 26.16% |
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
exo-cis-5,6-Dihydroxy-2-azabicyclo<2.2.1>heptan-3-one
Conditions | Yield |
---|---|
With potassium permanganate In acetone Inert atmosphere; | 25% |
acetic anhydride
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
(-)-(1S,4R)-4-acetamidocyclopent-2-enylmethanol
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
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