Structure of 255735-88-7
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 255735-88-7 |
Formula : | C8H18N2O2 |
M.W : | 174.24 |
SMILES Code : | O=C(OC(C)(C)C)NCC(N)C |
MDL No. : | MFCD09788609 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H317-H319 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.88 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 47.79 |
TPSA ? Topological Polar Surface Area: Calculated from |
64.35 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.21 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.42 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.86 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.63 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.03 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.82 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.85 |
Solubility | 24.3 mg/ml ; 0.14 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.34 |
Solubility | 7.99 mg/ml ; 0.0459 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.31 |
Solubility | 8.55 mg/ml ; 0.0491 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.06 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.54 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
tert-Butyl (2-aminoethyl) carbamate (17.3 mg, 0.1 mmol), sodiumtriacetoxyborohydride (64 mg, 0.3 mmol) and glacial acetic acid (17 IL, 0. 3 MMOL) were added to a solution of 113 (50 mg, 0.1 mmol) in DCM (1.0 ML) and the resulting mixture allowed to stir at r. t. for 18 h. The reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts were washed with brine, dried (MGS04), filtered, and the filtrate concentrated IN VACUO. The crude residue was treated with TFA/DCM (1: 1,2. 0 ML) and after 30 min the volatiles were evaporated in vacuo. Purification of the crude residue by preparative reversed phase HPLC on YMC Pack Pro C18 (gradient elution; 0-71percent ACETONITRILE/WATER as eluent, 0. 1percent TFA modifier) gave 114 as the trifluoroacetate salt. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 20 - 40℃; for 96h; | After 10% palladium carbon (100 mg) was added to a methanol (30 ml) solution of the compound (1.00 g) obtained in Referential Example 339, the resulting mixture was stirred at room temperature for 14 hours under a hydrogen atmosphere. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (20 ml). The compound (1.12 g) obtained in Referential Example 9, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.15 g) and 1-hydroxybenzotriazole (0.676 g) were added. After stirring overnight at room temperature, stirring was conducted further at 40C for 4 days. The reaction mixture was concentrated under reduced pressure. Chloroform was added to the residue. The resulting mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and saturated saline. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue purified by chromatography (methylene chloride:methanol = 98:2 ? 95:5) on a silica gel column, whereby the title compound (1.01 g) was obtained.1H-NMR(CDCl3) delta: 1.20(3H,d,J=6.6Hz), 1.44(9H,s), 3.29-3.41(1H,m), 3.42-3.51(1H,m), 3.91(1H,br s), 4.55(1H,br s), 7.71(1H,dd,J=9.0,2.4Hz), 7.99(1H,br s), 8.20(1H,d,J=9.0Hz), 8.31(1H,d,J=2.4Hz), 9.73(1H,s). MS(ESI)m/z: 357(M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 14h; | After 10percent palladium carbon (100 mg) was added to a methanol (30 ml) solution of the compound (1.00 g) obtained in Referential Example 339, the resulting mixture was stirred at room temperature for 14 hours under a hydrogen atmosphere. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (20 ml). The compound (1.12 g) obtained in Referential Example 9, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.15 g) and 1-hydroxybenzotriazole (0.676 g) were added. After stirring overnight at room temperature, stirring was conducted further at 40°C for 4 days. The reaction mixture was concentrated under reduced pressure. Chloroform was added to the residue. The resulting mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and saturated saline. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue purified by chromatography (methylene chloride:methanol = 98:2 --> 95:5) on a silica gel column, whereby the title compound (1.01 g) was obtained.1H-NMR(CDCl3) delta: 1.20(3H,d,J=6.6Hz), 1.44(9H,s), 3.29-3.41(1H,m), 3.42-3.51(1H,m), 3.91(1H,br s), 4.55(1H,br s), 7.71(1H,dd,J=9.0,2.4Hz), 7.99(1H,br s), 8.20(1H,d,J=9.0Hz), 8.31(1H,d,J=2.4Hz), 9.73(1H,s). MS(ESI)m/z: 357(M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; methanol; | (d) [(2R)-2-aminopropyl]carbamic acid, 1,1-dimethylethyl ester To a solution of the product from example 9, step (c) (3.8 g) in THF (100 ml) was added piperidine (5 ml) and the mixture allowed to stand for 1 hour at room temp. The mixture was evaporated to dryness and the residue purified (SiO2, 5percent methanol:dichloromethane as eluant) to give the subtitle compound as a colourless oil (1.7 g). NMR deltaH (CDCl3) 4.95 (1H, s), 3.13 (1H, m), 2.99 (1H, m), 2.87 (1H, m), 1.38 (9H, s), 1.08 (3H, d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation 12 To a solution of dl-1,2-diaminopropane (1.48 g, 20.0 mmol) and sodium carbonate (2.73 g, 22.0 mmol) in dioxane (100.0 mL) and water (100.0 mL) was added di-tert-dicarbonate (4.80 g, 22.0 mmol) at room temperature. The resulted mixture was stirred for 14 hr. Dioxane was removed in vacuo. The precipitate was filtered off and the filtrate was concentrated in vacuo to dryness. The residue was triturated with EtOAc and then filtered. The filtrate was concentrated in vacuo to dryness to give a mixture of dl-1-amino-2-(1,1-dimethylethoxy)carbonylamino-propane and dl-2-amino-1-(1,1-dimethylethoxy)carbonylamino-propane which were not separable by normal chromatography method. The mixture was used for the reaction in Example 8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | Example 1OA; tert-butyl {3-[(4-chlorobenzyl)amino]propyl}carbamate EPO <DP n="29"/>10 g (71.1 mmol) 4-chlorobenzaldehyde and 13.6 g (78.3 mmol) tert-butyl (2-aminopropyl)- carbamate are dissolved in 200 ml methanol and stirred for 2 h at room temperature. The solution is cooled to O0C and 13.5 g (355.7 mmol) sodium borohydride are carefully added. Water is added until a clear solution is formed and the mixture is stirred at room temperature overnight. The mixture is concentrated under vacuum, the residue is diluted with dichloromethane and the organic phase is washed with brine, dried over magnesium sulfate and concentrated under vacuum. The crude product is re-crystallized from petroleum ether to yield 8.9 g (42percent of th.) of the title compound as a solid.HPLC (method 6): R, = 4.03 min; MS (ESIpos): m/z = 299 (M+H)+1H-NMR (300 MHz, DMSOd6): delta = 7.35 (m, 4H), 6.70 (m, IH), 3.60 (s, 2H), 2.95 (m, 2H), 2.40 (m, 2H), 2.10 (bs, IH), 1.50 (m, 2H), 1.40 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With 1H-imidazole; dicyclohexyl-carbodiimide; In ethyl acetate; at 0 - 20℃; | To a solution of tert-butyl 2-aminopropylcarbamate (3.6 g, 20.6 mmol), 2-hydroxybenzoic acid (2.79 g, 20.6 mmol) and imidazole (1.41 g, 20.6 mmol) in EtOAc (100 mL) at 0° C. was slowly added a solution of DCC (4.26 g, 20.6 mmol) in EtOAc (50 mL). The reaction mixture was stirred (RT, 16 h), filtered and concentrated under reduced pressure. The crude product was purified by silica chromatography, EtOAc/Petroleum ether (0-20percent) to afford tert-butyl 2-(2-hydroxybenzamido)propylcarbamate (2.4 g, 40percent) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triethylamine; HATU; In acetonitrile; at 0 - 20℃; | Example 21; Preparation of N-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidopropyl)-2-hydroxybenzamide (14); To a solution of tert-butyl 2-aminopropylcarbamate (1.06 g, 6.09 mmol, prepared as previously described), DHA (2.0 g, 6.09 mmol) and Et3N (1.7 mL, 12.8 mmol) in CH3CN (40 mL) at 0° C. was added HATU (2.31 g, 6.09 mmol). The mixture was stirred (RT, 16 h) and concentrated under reduced pressure. The residue was diluted with brine (100 mL) and extracted with EA (2.x.100 mL). The combined organic layers were washed with saturated NaHCO3 (100 mL) and brine (100 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, eluting with EA-PE (0-25percent) to afford tert-butyl 2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidopropylcarbamate (2.1 g, 70percent) as a light yellow oil. Mass calculated for C30H48N2O3=484.71; found: [M+H]+=485.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.7% | With hydrogen;palladium over charcoal; In methanol; at 20℃; under 760.051 Torr; for 16h; | A mixture of afford tert-butyl 2-azidopropylcarbamate (7.0 g, 3.6 mmol) and Pd/C (0.7 g) in MeOH (250 mL) was stirred under a H2 (1 atm) atmosphere (RT, 16 h). The mixture was filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, eluting with saturated NH3 in MeOH-DCM (0-10percent) to afford tert-butyl 2-aminopropylcarbamate (5.1 g, 83.7percent) as a light yellow oil. 1HNMR (CDCl3): delta4.9 (bs, 1H, NH), 3.15 (m, 1H, CH), 3.0 (m, 1H, CH2), 2.8 (m, 1H, CH2), 1.7 (bs, 2H, NH2), 1.5 (s, 9H, CH3), 1.0 (d, 3H, CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 90℃; for 12h;Inert atmosphere; | Example 38A; tert-Butyl {2-[(5-cyanopyridin-2-yl)amino]propyl}carbamate 2-Chloro-5-cyanopyridine (477 mg, 3.4 mmol), tert-butyl (2-aminopropyl)carbamate (300 mg, 1.7 mmol) and potassium bicarbonate (345 mg, 3.4 mmol) are dissolved in DMF (10 ml) and stirred at 90° C. under argon for 12 h. The reaction mixture is diluted with water (100 ml) and extracted with ethyl acetate (3.x.75 ml). The combined organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. After removal of the solvent, the residue is purified by flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 10:1). 265 mg (55percent of theory) of the product are obtained as a solid.LCMS (method 4): Rt=3.21 min. (m/z=277 (M+H)+)1H-NMR (400 MHz, DMSO-d6): delta=8.37 (d, 1H), 7.66 (d, 1H), 7.37 (d, 1H), 6.87 (br t, 1H), 6.50 (d, 1H), 4.05 (m, 1H), 3.02 (m, 2H), 1.37 (s, 9H), 1.07 (d, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 120℃; for 12h;Inert atmosphere; | Example 36A; tert-Butyl (2-[7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}propyl)carbamate 5-Chloro-7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidine (Example 6A) (800 mg, 2.7 mmol), tert-butyl (2-aminopropyl)carbamate (700 mg, 4.0 mmol) and N,N-diisopropylethylamine (1.00 g, 8.0 mmol) are dissolved in DMSO (13 ml) and stirred at 120° C. under argon for 12 hours. The reaction mixture is diluted with water (100 ml) and extracted with ethyl acetate (3.x.75 ml). The combined organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. Removal of the solvent results in a foam which is taken up in diethyl ether. The product precipitates as solid from the diethyl ether solution and is filtered off with suction and dried. 800 mg (68percent of theory) of the product are obtained as a solid.LCMS (method 3): Rt=2.04 min. (m/z=437 (M+H)+)1H-NMR (400 MHz, DMSO-d6): delta=8.04 (s, 1H), 7.75 (dd, 1H), 7.70 (d, 1H), 7.56 (d, 1H), 7.51 (m, 2H), 7.10 (s, 1H), 6.96 (t, 1H), 4.34 (m, 1H), 3.21 (m, 2H), 1.32 (s, 9H), 1.23 (d, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; for 16h;Reflux; | (+/-)- ,2-diaminopropane (2.30 mL, 27.0 mmol) was dissolved in ethanol (100 mL) and 1 ,1-dimethy.ethyl phenyl carbonate (9.98 mL, 54.0 mmol) added. The mixture was heated to reflux for 16 hours, cooled to room temperature, and concentrated by rotovap. The residue was diluted with water before hydrochloric acid (1 M) was added carefully until the pH was ~3. The aqueous phase was washed 3 times withdichloromethane and then made strongly basic with sodium hydroxide (1 M). The aqueous phase and extracted 3 times with dichloromethane and the combined organic layers dried over sodium sulfate before being concentrated to give the title compound (2.98 g, 63percent) as a mixture (-85:15) of regioisomers. ES-LCMS m/z: 175 (M+1 ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.1% | With sodium tris(acetoxy)borohydride; 1,2-dichloro-ethane; at 0 - 20℃; for 2h; | To a stuffed solution of 3 -(3 ,3-diethyl- 1 -methoy-2-oxo- 1 -azaspiro [4.51 dec-7-en-8- yl)- 1 H-pyrrazole-4-carbaldehyde (0.58 g, 1.75 mmol) and tert-butyl(2- methylamino)ethyl)carbamate (0.495 g, 2.62mmol) in EDC (25 ml) was added sodium triacetoxy borohydride (1.11 g, 5.26 mmol) portionwise at 0 °C. The resulting mixture was stirred at rt for 2 h at which time the reaction mixture was diluted with water (30 ml) and extracted with ethyl acetate (2x20 ml) and the combined organic layers were dried over sodium sulphate. The solvent was removed under reduced pressure and the resulting crude was purified by column chromatography to give title compound (95.1percent) LCMS: mlz=504.4 [M+1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64.9% | With sodium tris(acetoxy)borohydride; In ethylene dibromide; at 20 - 60℃; for 1h; | To a stuffed solution of 3-(3,3-diethyl- 1 -methyl-2-oxo- 1 -azaspiro[4.5]dec-7-en-8- yl)-1H-pyrazole4)carbaldehyde(0. 1 g, 0.332 mmol) and tertbutyl(2methylamino)ethyl)carbamate (0.093 g, 0.497 mmol) in EDC (4 ml) at rt, were added sodium triacetoxy borohydride (0.210 g,0.995 mmol) in portion wise, stirred reaction 1 h at 60 °C. The reaction was diluted by water and extracted with DCM (2x15 ml), washed with sodium bicarbonate solution, the combined organic layers were dried over anhydrous sodium sulphate. The solvent was removed under reduced pressure and the resulting crude was purified by column chromatography using mobile phase 5percent methanol in dichloromethane to give title compound (64.9percent). LCMS: mlz=487.35 [M+1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.46% | With sodium tris(acetoxy)borohydride; In ethylene dibromide; at 50 - 55℃; for 2h; | To a 3-neck 10 ml RBF, 3- (4- ((2,2,2-trifluoroethoxy)methyl)cyclohex- 1-en-i -yl)1H-pyrazole-4-carbaldehyde (0.160 g, 0.55 mmol) and tert-butyl methyl(2-(methylamino)ethyl)carbamate (0.157 g, 0.83 mmol) was dissolved in ethylene dichloride (4 ml) at 5 °C temperature. Sodium triacetoxy borohydride (0.353 g, 1.66 mmol) was added portionwise. After addition, the ice bath was removed and reaction mixture was stirred at 50- 55 °C for 2 h. Sodium bicarbonate (sat. aq.) was added to reaction mixture and extracted by DCM (3x20 ml), dried over Na2504. The organic layers were concentrated and the crude product was purified by silica gel column chromatography using mobile phase 0-16percent ethyl acetate in hexane to get the title compound as a pale yellow liquid. (85.46percent). LCMS:mlz=46 1.66 [M+1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29.9% | With sodium tris(acetoxy)borohydride; In ethylene dibromide; at 0 - 55℃; for 2h; | To a 3-necked 25m1 RBF, 3-(3,3-dimethyl- 1 -oxaspiro[4.5]dec-7-en-8-yl)- 1H- pyrazole-4-carbaldehyde (0.240 g, 0.92 mmol) and tert-butyl (2- aminoethyl)(methyl)carbamate (0.241 g, 1.38 mmol) was dissolved in EDC (6 ml) at 0 °C. Sodium triacetoxy borohydride (0.586 g, 2.76 mmol) was added portionwise. After addition, the ice bath was removed and the reaction mixture was stuffed at 55 °C for 2 h. The reaction mixture was neutralized by sodium bicarbonate (sat. 20 ml) and extracted by DCM (3x25 ml), dried over Na2504. The solvent was evaporated to obtain crude product which was purified using silica column chromatography using mobile phase 0-2percent MeOH in DCM to afford the title compound as a thick pale yellow oil (29.9percent). LCMS: mlz=419.5 [M+1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.9% | To a stuffed solution of 3-( 1 ,5-diethyl-8-oxabicyclo[3 .2.11 oct-2-en-3-yl)- 1H- pyrazole-4-carbaldehyde (0.94 g, 3.61 mmol) in ethylene dichloride (10 ml) was added with tert-butyl (2-(dimethylamino)ethyl) (methyl)carbamate (1.01 g, 5.42 mmol) and stuffed it for 30 mm at room temperature. This was added with sodium triacetoxy borohydride (2.29 g,10.8 mmol) portionwise and stirred it for 1 h. Reaction mixture was basified with sodium bicarbonate until basic and extracted with DCM (3x50 ml). The combined organic layer was dried over anhydrous sodium sulphate and concentrated to obtain yellow sticky liquid product (92.9percent). LCMS: mlz=433.7 [M+1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.2 g | In dichloromethane; at 0 - 25℃; for 1h; | 10385] Step 1: To a solution of allyl carbonochloridate (1.66 g, 13.77 mmol, 1.46 mL, 3.00 equiv.) in DCM (10.00 mL) was added compound 1 (800.00 mg, 4.59 mmol, 1.00 equiv.) slowly at 0° C. The mixture was stirred at 25° C. for 1 hout The mixture was quenched by addition 10percent citric acid solution, and extracted with DCM (45 mE). The combined organic layers were dried over Na2SO4, and filtered. Concentration under reduced pressure resulted in 1 .2 g of compound 2. |
A103000 [121103-15-9]
(S)-tert-Butyl (2-aminopropyl)carbamate
Similarity: 1.00
A340304 [333743-54-7]
(R)-tert-Butyl (2-aminopropyl)carbamate
Similarity: 1.00
A183459 [1269493-35-7]
(S)-tert-Butyl (2-aminopropyl)carbamate hydrochloride
Similarity: 0.97
A164387 [100927-10-4]
(R)-tert-Butyl (1-aminopropan-2-yl)carbamate
Similarity: 0.95
A190139 [149632-73-5]
tert-Butyl (1-aminopropan-2-yl)carbamate
Similarity: 0.95
A103000 [121103-15-9]
(S)-tert-Butyl (2-aminopropyl)carbamate
Similarity: 1.00
A340304 [333743-54-7]
(R)-tert-Butyl (2-aminopropyl)carbamate
Similarity: 1.00
A183459 [1269493-35-7]
(S)-tert-Butyl (2-aminopropyl)carbamate hydrochloride
Similarity: 0.97
A164387 [100927-10-4]
(R)-tert-Butyl (1-aminopropan-2-yl)carbamate
Similarity: 0.95
A190139 [149632-73-5]
tert-Butyl (1-aminopropan-2-yl)carbamate
Similarity: 0.95
A103000 [121103-15-9]
(S)-tert-Butyl (2-aminopropyl)carbamate
Similarity: 1.00
A340304 [333743-54-7]
(R)-tert-Butyl (2-aminopropyl)carbamate
Similarity: 1.00
A183459 [1269493-35-7]
(S)-tert-Butyl (2-aminopropyl)carbamate hydrochloride
Similarity: 0.97
A164387 [100927-10-4]
(R)-tert-Butyl (1-aminopropan-2-yl)carbamate
Similarity: 0.95
A190139 [149632-73-5]
tert-Butyl (1-aminopropan-2-yl)carbamate
Similarity: 0.95