乙基 3-(二苯甲基氨基)丙酯

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Add titanium isopropoxide (860 mg, 3.03 mmol) to a solution of ethyl 3-(dibenzylamino)propanoate (9.0 g, 30.3 mmol) in ethyl ether, cool to 0° C., add ethyl magnesium bromide (3M in Et2O, 30.3 mL) drop-wise over 1 h, maintaining the temperature at ˜0-4° C., allow to warm to RT and stir overnight. Cool to 0° C., add satd. NH4Cl, stir at RT for 15 minutes, make basic with satd. NaHCO3 and extract with EtOAc (2×). Wash the combined organics with brine, dry over MgSO4, concentrate and purify via silica gel chromatography to give the title compound (7.5 g, 88%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.20-7.15 (m, 8H), 7.12-7.07 (m, 2H), 3.45 (s, 4H), 2.61-2.59 (m, 2H), 1.57 (t, J=5.6 Hz, 2H), 0.36-0.33 (m, 2H), 0.30-0.17 (m, 2H). maintaining the temperature at ˜0-4° C. to warm to RT Cool to 0° C. add NaHCO3 and extract with EtOAc (2×) Wash the combined organics with brine dry over MgSO4 concentrate purify via silica gel chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Heat a solution of ethyl 3-aminopropanoate hydrochloride (80.0 g, 0.52 mol), benzylbromide (186.7 g, 1.1 mol) and K2CO3 (179.4 g, 1.3 mol) in acetonitrile (1 L) at 40° C. overnight. Concentrate the mixture to dryness, treat with water, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate to dryness and purify via silica gel chromatography (Pet Ether/EtOAc, 50:1) to afford the title compound (150 g, 97% yield). 1H NMR (400 MHz, CDCl3): δ 7.35-7.21 (m, 10H), 4.09 (q, J=7.2 Hz, 2H), 3.58 (s, 4H), 2.82 (t, J=7.2 Hz, 2H), 2.50 (t, J=7.2 Hz, 2H), 1.21 (t, J=7.2 Hz, 3H). Concentrate the mixture to dryness treat with water extract with EtOAc (3×) wash the combined organics with brine dry over Na2SO4 concentrate to dryness purify via silica gel chromatography (Pet Ether/EtOAc, 50:1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Heat a solution of ethyl 3-aminopropanoate hydrochloride (80.0 g, 0.52 mol), benzylbromide (186.7 g, 1.1 mol) and K2CO3 (179.4 g, 1.3 mol) in acetonitrile (1 L) at 40° C. overnight. Concentrate the mixture to dryness, treat with water, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate to dryness and purify via silica gel chromatography chromatography (Pet Ether/EtOAc, 50:1) to afford the title compound (150 g, 97% yield). 1H NMR (400 MHz, CDCl3): δ 7.35-7.21 (m, 10H), 4.09 (q, J=7.2 Hz, 2H), 3.58 (s, 4H), 2.82 (t, J=7.2 Hz, 2H), 2.50 (t, J=7.2 Hz, 2H), 1.21 (t, J=7.2 Hz, 3H). Concentrate the mixture to dryness treat with water extract with EtOAc (3×) wash the combined organics with brine dry over Na2SO4 concentrate to dryness purify via silica gel chromatography chromatography (Pet Ether/EtOAc, 50:1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Heat a solution of ethyl 3-aminopropanoate hydrochloride (80.0 g, 0.52 mol), benzylbromide (186.7 g, 1.1 mol) and K2CO3 (179.4 g, 1.3 mol) in acetonitrile (1 L) at 40° C. overnight. Concentrate the mixture to dryness, treat with water, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate to dryness and purify via silica gel chromatography chromatography (Pet Ether/EtOAc, 50:1) to afford the title compound (150 g, 97% yield). 1H NMR (400 MHz, CDCl3): δ 7.35-7.21 (m, 10H), 4.09 (q, J=7.2 Hz, 2H), 3.58 (s, 4H), 2.82 (t, J=7.2 Hz, 2H), 2.50 (t, J=7.2 Hz, 2H), 1.21 (t, J=7.2 Hz, 3H). Concentrate the mixture to dryness treat with water extract with EtOAc (3×) wash the combined organics with brine dry over Na2SO4 concentrate to dryness purify via silica gel chromatography chromatography (Pet Ether/EtOAc, 50:1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Sodium carbonate (21.1 g, 199 mmol) was added to a suspension of fl-alanine ethyl ester hydrochloride (10.2 g, 66.4 mmol) and benzyl bromide (16.2 mL, 136 mmol) in acetonitrile (265 mL). The reaction mixture was stirred at ambient temperature overnight and then filtered through a layer of CELITE filter aid. The filter cake was rinsed with acetonitrile (100 mL). The filtrate was concentrated under reduced pressure to provide 20.28 g of ethyl 3-dibenzylaminopropionate as a pale yellow oil. filtered through a layer of CELITE filter aid The filter cake was rinsed with acetonitrile (100 mL) The filtrate was concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Sodium carbonate (21.1 g, 199 mmol) was added to a suspension of fl-alanine ethyl ester hydrochloride (10.2 g, 66.4 mmol) and benzyl bromide (16.2 mL, 136 mmol) in acetonitrile (265 mL). The reaction mixture was stirred at ambient temperature overnight and then filtered through a layer of CELITE filter aid. The filter cake was rinsed with acetonitrile (100 mL). The filtrate was concentrated under reduced pressure to provide 20.28 g of ethyl 3-dibenzylaminopropionate as a pale yellow oil. filtered through a layer of CELITE filter aid The filter cake was rinsed with acetonitrile (100 mL) The filtrate was concentrated under reduced pressure

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Titanium isopropoxide (860 mg, 3.03 mmol) was added to a solution of ethyl 3-(dibenzylamino)propanoate (9.0 g, 30.3 mmol) in Et2O, cooled to 0° C., treated drop-wise with ethyl magnesium bromide (3M in Et2O, 30.3 mL) over 1 h, maintaining the temperature at 0˜4° C., then allowed to warm to RT and stirred overnight. The mixture was cooled to 0° C., treated with satd. NH4Cl, stirred at RT for 15 minutes, made basic with satd. NaHCO3 and extracted with EtoAc (2×). The combined organics were washed with brine, dried over MgSO4, concentrated and purified via silica gel chromatograph to give 1-(2-(dibenzylamino)ethyl)cyclopropanol (7.5 g, 88%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.20-7.15 (m, 8 H), 7.12-7.07 (m, 2 H), 3.45 (s, 4 H), 2.61-2.59 (m, 2 H), 1.57 (t, J=5.6 Hz, 2 H), 0.36-0.33 (m, 2 H), 0.30-0.17 (m, 2 H). maintaining the temperature at 0˜4° C. to warm to RT The mixture was cooled to 0° C. treated with satd NaHCO3 and extracted with EtoAc (2×) The combined organics were washed with brine dried over MgSO4 concentrated purified via silica gel chromatograph

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Titanium isopropoxide (860 mg, 3.03 mmol) was added to a solution of ethyl 3-(dibenzylamino)propanoate (9.0 g, 30.3 mmol) in Et2O, cooled to 0° C., treated drop-wise with ethyl magnesium bromide (3M in Et2O, 30.3 mL) over 1 h, maintaining the temperature at 0˜4° C., then allowed to warm to RT and stirred overnight. The mixture was cooled to 0° C., treated with satd. NH4Cl, stirred at RT for 15 minutes, made basic with satd. NaHCO3 and extracted with EtoAc (2×). The combined organics were washed with brine, dried over MgSO4, concentrated and purified via silica gel chromatograph to give 1-(2-(dibenzylamino)ethyl)cyclopropanol (7.5 g, 88%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.20-7.15 (m, 8 H), 7.12-7.07 (m, 2 H), 3.45 (s, 4 H), 2.61-2.59 (m, 2 H), 1.57 (t, J=5.6 Hz, 2 H), 0.36-0.33 (m, 2 H), 0.30-0.17 (m, 2 H). maintaining the temperature at 0˜4° C. to warm to RT The mixture was cooled to 0° C. treated with satd NaHCO3 and extracted with EtoAc (2×) The combined organics were washed with brine dried over MgSO4 concentrated purified via silica gel chromatograph

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Titanium isopropoxide (860 mg, 3.03 mmol) was added to a solution of ethyl 3-(dibenzylamino)propanoate (9.0 g, 30.3 mmol) in Et2O, cooled to 0° C., treated drop-wise with ethyl magnesium bromide (3M in Et2O, 30.3 mL) over 1 h, maintaining the temperature at 0˜4° C., then allowed to warm to RT and stirred overnight. The mixture was cooled to 0° C., treated with satd. NH4Cl, stirred at RT for 15 minutes, made basic with satd. NaHCO3 and extracted with EtoAc (2×). The combined organics were washed with brine, dried over MgSO4, concentrated and purified via silica gel chromatograph to give 1-(2-(dibenzylamino)ethyl)cyclopropanol (7.5 g, 88%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.20-7.15 (m, 8 H), 7.12-7.07 (m, 2 H), 3.45 (s, 4 H), 2.61-2.59 (m, 2 H), 1.57 (t, J=5.6 Hz, 2 H), 0.36-0.33 (m, 2 H), 0.30-0.17 (m, 2 H). maintaining the temperature at 0˜4° C. to warm to RT The mixture was cooled to 0° C. treated with satd NaHCO3 and extracted with EtoAc (2×) The combined organics were washed with brine dried over MgSO4 concentrated purified via silica gel chromatograph

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of ethyl 3-aminopropanoate hydrochloride (80.0 g, 0.52 mol), benzylbromide (186.7 g, 1.1 mol) and K2CO3 (179.4 g, 1.3 mol) in MeCN (1 L) was heated at 40° C. overnight. The mixture was concentrated to dryness, poured into water, extracted with EtOAc (3×) and the combined organics were washed with brine, dried over Na2SO4 and purified via silica gel chromatography to give ethyl 3-(dibenzylamino)propanoate (150 g, 97%). The mixture was concentrated to dryness poured into water extracted with EtOAc (3×) the combined organics were washed with brine dried over Na2SO4 purified via silica gel chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Sodium carbonate (21.1 g, 199 mmol) was added to a suspension of β-alanine ethyl ester hydrochloride (10.2 g, 66.4 mmol) and benzyl bromide (16.2 mL, 136 mmol) in acetonitrile (265 mL). The reaction mixture was stirred at ambient temperature overnight and then filtered through a layer of CELITE filter aid. The filter cake was rinsed with acetonitrile (100 mL). The filtrate was concentrated under reduced pressure to provide 20.28 g of ethyl 3-dibenzylaminopropionate as a pale yellow oil. filtered through a layer of CELITE filter aid The filter cake was rinsed with acetonitrile (100 mL) The filtrate was concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Sodium carbonate (21.1 g, 199 mmol) was added to a suspension of β-alanine ethyl ester hydrochloride (10.2 g, 66.4 mmol) and benzyl bromide (16.2 mL, 136 mmol) in acetonitrile (265 mL). The reaction mixture was stirred at ambient temperature overnight and then filtered through a layer of CELITE filter aid. The filter cake was rinsed with acetonitrile (100 mL). The filtrate was concentrated under reduced pressure to provide 20.28 g of ethyl 3-dibenzylaminopropionate as a pale yellow oil. filtered through a layer of CELITE filter aid The filter cake was rinsed with acetonitrile (100 mL) The filtrate was concentrated under reduced pressure