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Product Details of [ 85909-08-6 ]

CAS No. :85909-08-6 MDL No. :MFCD00674099
Formula : C9H15NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :GJJYYMXBCYYXPQ-UHFFFAOYSA-N
M.W : 185.22 Pubchem ID :379000
Synonyms :

Calculated chemistry of [ 85909-08-6 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.78
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.99
TPSA : 46.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.2
Log Po/w (XLOGP3) : 1.34
Log Po/w (WLOGP) : 1.16
Log Po/w (MLOGP) : 0.45
Log Po/w (SILICOS-IT) : 0.86
Consensus Log Po/w : 1.2

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.63
Solubility : 4.3 mg/ml ; 0.0232 mol/l
Class : Very soluble
Log S (Ali) : -1.92
Solubility : 2.22 mg/ml ; 0.012 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.11
Solubility : 14.2 mg/ml ; 0.0767 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.99

Safety of [ 85909-08-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 85909-08-6 ]

* 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.

  • Upstream synthesis route of [ 85909-08-6 ]
  • Downstream synthetic route of [ 85909-08-6 ]

[ 85909-08-6 ] Synthesis Path-Upstream   1~23

  • 1
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  • [ 75178-87-9 ]
Reference: [1] Angewandte Chemie - International Edition, 2009, vol. 48, # 7, p. 1324 - 1327
[2] Chemistry - An Asian Journal, 2018, vol. 13, # 17, p. 2559 - 2565
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  • [ 67-56-1 ]
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  • [ 75178-87-9 ]
  • [ 85909-04-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2009, vol. 48, # 7, p. 1324 - 1327
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  • [ 85909-08-6 ]
  • [ 67-63-0 ]
  • [ 1140511-02-9 ]
  • [ 75178-87-9 ]
Reference: [1] Angewandte Chemie - International Edition, 2009, vol. 48, # 7, p. 1324 - 1327
  • 4
  • [ 67-56-1 ]
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  • [ 85909-04-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 22, p. 5395 - 5399
[2] Journal of Organic Chemistry, 1983, vol. 48, # 14, p. 2424 - 2426
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  • [ 67-56-1 ]
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  • [ 85909-04-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2009, vol. 48, # 7, p. 1324 - 1327
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  • [ 67-56-1 ]
  • [ 64-17-5 ]
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  • [ 85909-04-2 ]
  • [ 228110-66-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 22, p. 5395 - 5399
  • 7
  • [ 85909-08-6 ]
  • [ 100-58-3 ]
  • [ 116437-41-3 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: at -78℃; for 2 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water
Step A: Preparation of (4-oxo-4-phenylbutyl')-carbamic acid tert-butyl ester: To a solution of 2-oxo-pyrrolidine-l-carboxylic acid tert-butyl ester (7.03 g, 38 mmol) in THF (130 mL) was added phenylmagnesium bromide (1.0 M solution, 50 mL) at -78 °C. After stirring for 2 hour at -78 °C, HCl (2 M, 35 mL) was added to quench the reaction, which was then warmed to room temperature and the aqueous layer was extracted with EtOAc (2 x 100 mL). The combined organics were washed with brine (50 mL) and dried over Na2SO4, filtered and concentrated under reduced pressure to afford 9.56 g (96percent yield) of the desired product.
60.6%
Stage #1: at -78℃; for 0.666667 h;
Stage #2: With water In tetrahydrofuran
Phenylmagnesium bromide 1M in THF solution (31.9 mL, 31.0 mmol) (Aldrich) was added to a solution of tert-butyl 2-oxopyrrolidine-1-carboxylate (5.0 g, 24.3 mmol) (Aldrich) in THF (100 mL) at -78° C. Mixture was stirred at -78° C. for 40 minutes and then poured into brine. The aqueous phase was extraced with ethyl acetate (2.x.) and the combined organic phase was dried (magnesium sulfate), filtered, and concentrated. The residue was purified by flash chromatography eluting with 5-40percent ethyl acetate in hexanes to give tert-butyl 4-oxo-4-phenylbutylcarbamate. (Yield 4.31 g, 60.6percent).
Reference: [1] Patent: WO2006/44825, 2006, A2, . Location in patent: Page/Page column 55
[2] Patent: US2012/184542, 2012, A1, . Location in patent: Page/Page column 109
[3] Organic Letters, 2011, vol. 13, # 16, p. 4348 - 4351
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  • [ 108-86-1 ]
  • [ 85909-08-6 ]
  • [ 116437-41-3 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 16, p. 4215 - 4218
[2] Journal of Organic Chemistry, 1989, vol. 54, # 1, p. 228 - 234
  • 9
  • [ 85909-08-6 ]
  • [ 116437-41-3 ]
Reference: [1] Organic Letters, 2003, vol. 5, # 22, p. 4227 - 4230
[2] Journal of the American Chemical Society, 2006, vol. 128, # 7, p. 2224 - 2225
  • 10
  • [ 85909-08-6 ]
  • [ 86953-79-9 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2014, vol. 62, # 6, p. 1233 - 1239
  • 11
  • [ 616-45-5 ]
  • [ 24424-99-5 ]
  • [ 85909-08-6 ]
YieldReaction ConditionsOperation in experiment
96% With dmap; triethylamine In acetonitrile at 0 - 20℃; To a solution of pyrrolidin-2-one (10.0 g, 118 mmol) in CH3CN (118 mL) were added TEA (19.6 mL, 141 mmol), DMAP (7.18 g, 58.8 mmol) and (t-Boc)2O (32.7 mL, 141 mmol) at 0° C.
The reaction mixture was stirred at room temperature overnight and then partitioned between EtOAc and water.
The separated organic layer was washed with 1 N aq. HCl, 1 N aq. NaOH and brine, dried over Na2SO4, filtered and concentrated in vacuo.
The residue was purified by column chromatography on SiO2 (Hex:EtOAc=1:1) to afford tert-butyl 2-oxopyrrolidine-1-carboxylate (21.0 g, 96percent) as a pale yellow oil. 1H-NMR (CDCl3, Varian, 400 MHz): δ 1.53 (9H, s), 2.00 (2H, quint, J=8.0 Hz), 2.52 (2H, t, J=8.0 Hz), 3.75 (2H, t, J=7.6 Hz).
95.3% at 25℃; for 8.5 h; 2.55 g (30.0 mmol) of 2-pyrrolidinone, 25.5 g of toluene and 0.37 g (3.0 mmol) of N,N-dimethylaminopyridine were added, and the temperature of the mixture was adjusted to 25°C. Into the resultant solution, a solution composed of 8.50 g (39.0 mmol) of di-tert-butyl dicarbonate and 2.55 g of toluene was dropped over a period of 30 minutes, and the mixture was thermally insulated at 25°C for 8 hours. To the resultant solution was added 10.9 g of 1percent hydrochloric acid and mixed, then, liquid-partitioning was caused. The resultant organic layer was washed with 5.0 g of a 5percent sodium hydrogen carbonate aqueous solution, then, further washed with 5.0 g of water. The resultant organic layer was concentrated under reduced pressure, to obtain 5.70 g of an oily substance containing 5.30 g (28.6 mmol) of N-tert-butoxycarbonyl-2-pyrrolidinone. The yield of N-tert-butoxycarbonyl-2-pyrrolidinone with respect to 2-pyrrolidinone was 95.3percent. The determinate quantity of N-tert-butoxycarbonyl-2-pyrrolidinone was obtained by gas chromatography. As the column, DB-5 (0.53 mmφ x 30 m, 1.5 μm) manufactured by JJ was used.
95% With dmap In acetonitrile at 20℃; for 4 h; At 0 C, to a stirred solution of pyrrolidinone 9 (3.83 mL,50.0 mmol, 1.0 eq.) in MeCN (100 mL) was added Boc2O (13.09 g,60.0 mmol, 1.2 eq.) and DMAP (0.61 g, 5.0 mmol, 10 molpercent). The reaction mixture was warmed to room temperature and stirred for 4 h. The reaction mixture was concentrated in vacuo, dissolved in EtOAc (200 mL), washed with 0.025 M aq. HCl (200 mL), and backextracted with EtOAc (200 mL). The combined organic layers were washed with brine (400 mL), dried over MgSO4, filtered, andconcentrated in vacuo to afford the crude product which was purifiedby flash column chromatography (c-Hex/EtOAc; 1:1) affordingthe title compound (8.81 g, 95percent) as an orange oil. Rf 0.3 (c-Hex/EtOAc; 1:1); 1H NMR (CDCl3, 300 MHz): d 1.53 (s, 9H), 2.00 (quin,J 8.0 Hz, 2H), 2.51 (t, J 8.0 Hz, 2H), 3.75 (t, J 8.0 Hz, 2H).
94% With dmap In acetonitrile at 20℃; for 1 h; Example 112 Atert-butyl 2-oxopyrrolidine-1-carboxylate; To a solution of 2-pyrrolidinone (10.82 g, 127 mmol) in acetonitrile (400 mL) was added DMAP (1.53 g, 12.6 mmol) followed by a solution of 33.6 g of di-tert-butyldicarbonate (77.1 mmol) in 20 mL of acetonitrile. The colorless reaction mixture was stirred at room temperature for 1 h. The resulting dark yellow reaction mixture was concentrated by rotary evaporation in vacuo and the resulting oil was taken up in diethyl ether. The mixture was washed with an aqueous solution of 1N HCl and a saturated aqueous brine solution. The organic phase was dried over sodium sulfate, and concentrated by rotary evaporation in vacuo to afford a yellow oil. Purification by gradient column chromatography on triethylamine washed silica gel (5:1-->3:1-->1:1 petroleum ether:ethyl acetate) afforded tert-butyl 2-oxopyrrolidine-1-carboxylate as a pale yellow semi-solid (22.2 g, yield 94percent). 1H-NMR (400 MHz, CDCl3) δ (ppm): 3.61 (t, J=7.3 Hz, 2H), 2.36 (t, J=7.9 Hz, 2H), 1.86 (tt, J=7.9 Hz, 7.3 Hz, 2H), 1.38 (s, 9H); LC-MS (ESI) m/z: 208 (M+Na)+.
94% With dmap In acetonitrile at 0 - 20℃; for 2.5 h; Pyrrolidinone (8.04 g, 94.6 mmol) was diluted in MeCN (50 mL). The solution was cooled to 0 °Cbefore the addition of Boc2O (21.9 g, 100 mmol, 1.05 eq.) and DMAP (1.09 g, 8.92 mmol, 0.94 eq.).The mixture was stirred at 0 °C for 30 min and a further 2 h at rt. The mixture was diluted in EtOAc(100 mL) and the reaction quenched with HCl (1M, 200 mL). The phases were separated and theaqueous phase was extracted with EtOAc (2 × 150 mL). The organic extracts were combined, washedwith brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo. The slightly orange oil(16.5 g, 94percent) was used into the next step without further purification. 1H NMR data matches withliterature precedent.1H NMR (500 MHz, CDCl3): 3.74 (2H, t, J 7.1, 5-H2), 2.50 (2H, t, J 8.1, 3-H2), 1.99 (2H, app quint, J 7.7,4-H2), 1.52 (9H, s, -tBu).
93% With dmap; triethylamine In dichloromethane at 20℃; [378] To a suspension of pyrrolidin-2-one (25.00 g, 0.29 mol) in DCM (500 mL) was added DMAP (3.59 g, 29.38 mmol), Et3N (61.5 mL, 0.44 mol) and B0C2O (75.0 mL, 0.32 mol). The mixture was stirred at room temperature overnight, then washed with water (100 mL) followed by saturated brine (100 mLx2). The separated organic phase was dried over anhydrous a2SC , filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) =1/1) to give the title compound as yellow liquid (51.0 g, 93percent). MS (ESI, pos. ion) m z: 130.1 [(M-C4H8)+H]+; 1H NM (400 MHz, CDCI3) δ (ppm): 3.76-3.71 (m, 2H), 2.50 (t, J= 8.1 Hz, 2H), 2.03-1.94 (m, 2H), 1.51 (s, 9H).
93% With dmap; triethylamine In dichloromethane at 20℃; Step 1) tert-butyl 2-oxopyrrolidine-l-carboxylate [0390] To a suspension of pyrrolidin-2-one (25.00 g, 0.29 mol) in DCM (500 mL) were added DMAP (3.59 g, 29.38 mmol), Et3N (61.5 mL, 0.44 mol) and Boc20 (75.0 mL, 0.32 mol) and the resulting mixture was stirred at room temperature overnight. Then the mixture was washed with water (100 mL) followed by brine (100 mL x 2), and then dried over anhydrous Na2SC>4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v) = 1/1) to give the title compound as yellow liquid (51.0 g, 93percent). MS (ESI, pos. ion) m/z: 130.1 [M-56+H]+; NMR (400 MHz, CDCb): δ (ppm) 3.76-3.71 (m, 2H), 2.50 (t, J= 8.1 Hz, 2H), 2.03-1.94 (m, 2H), 1.51 (s, 9H).
93% With dmap; triethylamine In dichloromethane at 20℃; To a solution of pyrrolidin-2-one (25.00 g, 0.29 mol) in DCM (500 mL) DMAP (3.59 g, 29.38 mmol), Et3N (61.5 mL, 0.44 mol) and Boc2O (75.0 mL, 0.32 mol) were added to give a reaction system. The resulting reaction was stirred at ambient temperature overnight. After the reaction was completed, the reaction mixture was washed with water (100 mL), brine (100 mL × 2), dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. Then, the resulting residue was subjected to silica gel column chromatography (PE / EtOAc (v / v) = 1/1) to give the title compound as a yellow liquid (51.0 g, 93percent).
93% With dmap; triethylamine In dichloromethane at 20℃; Pyrrolidin-2-one (25.00 g, 0.29 mol) was dissolved in dichloromethane (500 mL) and 4-dimethylaminopyridine (3.59 g, 29.38 mmol), triethylamine (61.5 mL, 0.44 mol) and Boc2O (75.0 mL, 0.32 mol) and the resulting reaction mixture was stirred overnight at room temperature then washed with water (100 mL) and brine (100 mL x 2), respectively. The separated organic phase is dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 1/1) to give the title compound as a yellow liquid (51.0 g, 93percent).
90.3% With dmap In dichloromethane at 20℃; for 12 h; To a stirred solution of compound 1a (10.0 g, 117 mmol, 1.0 equiv.) in DCM, (Boc)2O (25.5 g, 117 mmol, 1.00 equiv.) and DMAP (0.022 g, 0.180 mmol, 0.001 equiv.) were added at RT and stirred for 12 h. After consumption of the starting material (monitored by TLC), volatiles were removed under reduced pressure to afford compound 2a (19.6 g, 90.3percent) as a brown syrup. TLC: 50percent EtOAc/Hexane (Rf: 0.40)
1H NMR (400 MHz, CDCl3): δ 3.74 (t, J=6.8 Hz, 2H), 2.50 (t, J=8.0 Hz, 2H), 2.01 (t, J=7.6 Hz, 2H), 1.52 (s, 9H)
90.3% With dmap In dichloromethane at 20℃; for 12 h; To a stirred solution of compound la(10.0 g, 117 mmol, 1.0 equiv) in CH2C12, were added (Boc)20 (25.5 g, 117 mmol, 1.00 equiv) and DMAP (0.022 g, 0.180 mmol, 0.00 1 equiv) at room temperature and the resulting mixture was stirred for 12 hr. After consumption of the starting material (monitored by TLC), volatiles were removed under reduced pressure to afford compound 2a (19.6 g, 90.3percent) as a brown symp.TLC: 50percent EtOAc/Hexane (Rf: 0.40).NMR Spectroscopy: li-I NMR (400 M1-Iz. CDC13): ö 374 (t, J 6.8 I-Iz, 2H), 250 (t. J 8.0 Hz, 2H), 2.01 (t, J 7.6 Hz, 2H), 1.52 (s, 9H).
86% With dmap; triethylamine In dichloromethane at 20℃; for 12 h; Inert atmosphere To a solution of 2-pyrrolidinone(8.51 g, 100 mmol, 1.0 eq) in DCM (200 mL) were added DMAP(12.2 g, 100 mmol, 1.0 eq), Et3N (13.8 mL, 100 mmol, 1.0 eq), di-tertbutyldicarbonate (Boc2O) (43.65 g, 200 mmol, 2.0 eq). CO2 wasreleased from the stirring solution. The reaction mixture was stirredat room temperature for 12 h. The solvent was then evaporatedunder reduced pressure and the residual product was purified bysilica gel chromatography (petroleum ether/EtOAc 4/1) to affordN-boc-2-pyrrolidone as a white solid. Yield: 86percent; 1H NMR(500 MHz, CDCl3) δH (ppm): 3.72 (t, J = 7.0 Hz, 2H), 2.48 (t,J = 8.2 Hz, 2H), 1.94-2.01 (m, 2H), 1.50 (s, 9H); 13C NMR (125 MHz,CDCl3) δC (ppm): 174.3, 150.2, 82.7, 46.5, 32.9, 28.0, 17.4; ESI-MS: m/z 208.1 ([M+Na]+).
84% With dmap In acetonitrile at 20℃; for 14 h; To a solution of 2-pyrrolidone (5.99 g, 70.38 mmol, 1 equiv) in CH3CN (130 mL) were added successively (Boc)2O (18.43 g, 84.46 mmol, 1.2 equiv) and DMAP (0.86 g, 7.04 mmol, 0.1 equiv) at room temperature. The reaction mixture was stirred at this temperature for 14 h then the solvent was removed in vacuo. The crude material was taken up in EtOAc (100 mL) and washed with brine (100 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The resulting material was purified by column chromatography using a gradient elution (EtOAc/PE, 1:1 to 2:1) to provide N-tert-butoxycarbonylpyrrolidinone 6 (11.01 g, 84percent) as a pale yellow oil; Rf=0.45 (Et2O/PE, 1:20); 1H NMR (300 MHz): δ 3.74 (t, J=7.7, 2H), 2.51 (t, J=8.0, 2H), 2.00 (m, 2H), 1.94 (s, 9H); 13C NMR (75 MHz): δ 174.5, 150.3, 82.9, 46.7, 33.2, 28.3 (3C), 17.7.
83% With dmap; triethylamine In dichloromethane for 72 h; To a solution of 2-pyrrolidinone (3 g, 35.3 mmol) in DCM (80 ml) was added sequentially triethylamine (4.9 ml, 35.3 mmol), di- tert-buty\\ dicarbonate (15.4 g, 70.6 mmol), and 4- dimethylaminopyridine (4.3 g, 35.3 mmol). The reaction mixture was stirred over 3 days, the solvents removed and the crude material purified by flash chromatography using a Biotage SP4 (ethyl acetate/methanol gradient) to give the product as a yellow oil (5.4 g, 83percent). 1H NMR (400 MHz, CHLOROFORM-^) δ ppm 1.51 (s, 9 H), 1.93 - 2.04 (m, 2 H), 2.45 - 2.54 (m, 2 H), 3.68 - 3.77 (m, 2 H); Rf(1 :9 MeOH/EtOAc) = 0.6.
75% With dmap In acetonitrile at 20℃; for 2 h; A mixture of 2-pyrrolidone (1.0 ml, 10.5 mmol), di-tert-butyl dicarbonate (4.6 g, 21.0 mmol), and 4-(dimethylamino)pyridine (5.1 g, 42.0 mmol) was dissolved in acetonitrile (50 ml), and the obtained solution was stirred at a room temperature for 2 hours. The reaction solution was poured into a saturated ammonium chloride aqueous solution, and the obtained solution was then extracted with ethyl acetate. The extract was washed with a saturated ammonium chloride aqueous solution and with a saturated saline solution. The resultant was dried over anhydrous sodium sulfate, and was then concentrated, so as to obtain a crude product of 2-oxopyrrolidin-1-carboxylic acid tert-butyl (1.7 g, 75percent) in the form of a reddish brown substance.
68% With dmap; triethylamine In acetonitrile at 20℃; for 3 h; Inert atmosphere Boc20 (2.63 g, 12.05 mmol, 2.05 equiv) diluted was added to a solution pyrrolidinone (500.0 mg, 6.88 mmol, 1 equiv) and DMAP (754.0 mg, 6.1 7 mmol, 1 .05 equiv) in a mixture of triethylamine-acetonitrile (3:1 ) (20 mL) under argon at room temperature. After 3 h, the reaction mixture was diluted with EtOAc. The organic layer was washed successively with HCI (1 M), saturated aqueous sodium hydrogen carbonate solution and brine. After drying over MgS04, concentration of the solvent gave a residue, which was purified by flash chromatography (EtOAc neat) to afford the pure desired carbamate (743.0 mg, 4.01 mmol, 68percent) as a pale yellow oil (analyses in accordance with the literature data) (Banfi, L ; Basso, A. ; Cerulli, V. ; Guanti, G.; Riva, R. J. Org. Chem. 2008, 73, 1 608-161 1 ).
64% at 20℃; for 1 h; To a solution of 2-pyrrolidinone (10.82 g, 127 mmol) in acetonitrile (400 mL) was added DMAP (1.53 g, 12.6 mmol), followed by a solution of di-tert-butyldicarbonate (33.6 g, 77.1 mmol) in acetonitrile (20 mL). The reaction mixture was stirred at room temperature for 1 h. The resulting mixture was concentrated in vacuo and the resulting oil was taken up in diethyl ether. The mixture was washed consecutively with 1 N HCl and brine. The organic phase was dried over sodium sulfate, and concentrated in vacuo to afford the title compound as a yellow oil (15 g, 64percent) which was used directly in the next step
64% With dmap In acetonitrile at 20℃; for 1 h; Example 145 A/er/-Butyl 2-oxopyrrolidine- 1 -carboxylate[00811] To a solution of 2-pyrrolidinone (10.82 g, 127 mmol) in acetonitrile (400 mL) was added DMAP (1.53 g, 12.6 mmol), followed by a solution of di-tert- butyldicarbonate (33.6 g, 77.1 mmol) in acetonitrile (20 mL). The reaction mixture was stirred at room temperature for 1 h. The resulting mixture was concentrated in vacuo and the resulting oil was taken up in diethyl ether. The mixture was washed consecutively with 1 N HCl and brine. The organic phase was dried over sodium sulfate, and concentrated in vacuo to afford the title compound as a yellow oil (15 g, 64percent) which was used directly in the next step.
55% With dmap; triethylamine In dichloromethane at 20℃; for 8 h; g (11.7 mmol) of 2- pyrolidinone was dissolved in 15 mL of dichloromethane, and then 2.5 mL (17.8 mmol) of triethylamine and 107 mg (0.87 mmol) of dimethy- laminopyridine and 2.7 g (12.3 mmol) of di-t-butyl dicarbonate were added thereto. The reaction soilution was stirred at room temperature for 8 hours. 100 mL of ethylacetate was added to the solution, and the reaction solution was washed with water, and then an organic layar was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and then the residue was purified by column chromatographyto give 1.2 g (6.47 mmol) of the title compound in a yield of 55percent.[314] NMR: 1H-NMR(CDCl3) δ 3.76-3.73(2H, m), 2.53~2.49(2H, m), 2.04-1.88(2H, m),1.53 (9H, s)[315] Mass(EI) 186(M++.)
93% With dmap In dichloromethane Preparation of N-tert-Butyloxycarbonyl-2-pyrrolidinone
A solution of di-tert-butyl dicarbonate (28.2 g, 129 mmol) in dry CH2 Cl2 (80 mL) is added to a stirred solution of 2-pyrrolidinone (10.0 g, 117 mmol) and DMAP (200 mg, catalytic amount) in dry CH2 Cl2 (230 ml,) over 10 minutes.
After 16 hours, the solution is diluted with H2 O (150 mL) and extracted with EtOAc (4*100 mL).
The organic layers are combined, dried over anhydrous Na2 SO4, filtered, and concentrated under reduced pressure to give a red oil.
The oil is purified by silica gel chromatography (200 g SG, 40percent EtOAc/hexane) to yield 20.1 g (93percent) of the title compound as a gold oil.
IR (liq.) 2980, 1786, 1752, 1714, 1459, 1394, 1368, 1315, 1256, 1228, 1154, 1045, 1018, 858, 778 cm-1;
1 H NMR (300 MHz, CDCl3) δ 3.74, 2.50, 1.90-2.05, 1.52; MS (FAB) m/z 186, 131, 130, 112, 86, 57, 41.
93% With dmap In dichloromethane Step 1.
Preparation of N-tert-Butyloxycarbonyl-2-pyrrolidinone.
A solution of di-tert-butyl dicarbonate (28.2 g, 129 mmol) in dry CH2Cl2 (80 mL) is added to a stirred solution of 2-pyrrolidinone (10.0 g, 117 mmol) and DMAP (200 mg, catalytic amount) in dry CH2Cl2 (230 mL) over 10 minutes.
After 16 hours, the solution is diluted with H2O (150 mL) and extracted with EtOAc (4 x 100 mL).
The organic layers are combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give a red oiL The oil is purified by silica gel chromatography (200 g SG, 40percent EtOAc/hexane) to yield 20.1 g (93percent) of the title compound as a gold oil.

IR (liq.) 2980, 1786, 1752, 1714, 1459, 1394, 1368, 1315, 1256, 1228, 1154, 1045, 1018, 858, 778 cm-1;

1H NMR (300 MHz, CDCl3) δ 3.74, 2.50, 1.90-2.05, 1.52; MS (FAB) m/z 186, 131, 130, 112, 86, 57, 41.
73 g With dmap In acetonitrile at 0 - 35℃; Di-tert-butyldicarbonate (154 g, 154mL, 704 mmol) was added to solution of 2- Pyrrolidinone (50 g, 587 mmol) and DMAP (36 g, 293.7 mmol) in acetonitrile (500mL) at 0-5°C and stirring was continued at 20-35°C for 2 h. Reaction mixture was concentrated under reduced pressure to afford the residue, which was diluted with EtOAc, washed it with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 73 g of the title compound.
73 g With dmap In acetonitrile at 0 - 35℃; for 2 h; Di-tert-butyldicarbonate (154 g, 154 mL, 704 mmol) was added to solution of 2-Pyrrolidinone (50 g, 587 mmol) and DMAP (36 g, 293.7 mmol) in acetonitrile (500 mL) at 0-5° C. and stirring was continued at 20-35° C. for 2 h.
Reaction mixture was concentrated under reduced pressure to afford the residue, which was diluted with EtOAc, washed it with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 73 g of the title compound.
73 g With dmap In acetonitrile at 0 - 35℃; for 2 h; Di-tert-butyldicarbonate (154 g, 154 mL, 704 mmol) was added to solution of 2-Pyrrolidinone (50 g, 587 mmol) and DMAP (36 g, 293.7 mmol) in acetonitrile (500 mL) at 0-5° C. and stirring was continued at 20-35° C. for 2 h. Reaction mixture was concentrated under reduced pressure to afford the residue, which was diluted with EtOAc, washed it with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 73 g of the title compound.
73 g With dmap In acetonitrile at 0 - 35℃; for 2 h; Di-tert-butyldicarbonate (154 g, 154 mL, 704 mmol) was added to solution of 2-Pyrrolidinone (50 g, 587 mmol) and DMAP (36 g, 293.7 mmol) in acetonitrile (500 mL) at 0-5° C. and stifling was continued at 20-35° C. for 2 h. Reaction mixture was concentrated under reduced pressure to afford the residue, which was diluted with EtOAc, washed it with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 73 g of the title compound
25 g With dmap In acetonitrile at 0 - 20℃; for 16 h; To a solution of pyrrolidone (20.0 g, 235.0 mmol) in CH3CN (200 mL) were added (Boc)20(54.4 mL, 244.4 mmol) and DMAP (2.86 g, 23.5 mmol) at 0 °C. The reaction mixture wasstirred at room temperature for 16 h. The reaction mixture was concentrated under reducedpressure. Purification of the evaporation residue by flash chromatography (EtOAc / petroleum ether) afforded 25 g of tert-butyl 2-oxopyrrolidine- 1 -carboxylate as yellow oil.
215.5 g With dmap In acetonitrile at 0 - 35℃; for 2 h; At 0 to 5°C,To 2-pyrrolidone (100g)And DMAP (72g) in acetonitrile (1.0L)Di-tert-butyl dicarbonate (308 g) was added to the solution.And stirred at 20-35 °C for 2 h.The reaction mixture is concentrated under reduced pressure,Get residue,Diluted it with ethyl acetate,Wash with water,Dry with anhydrous sodium sulfatefilter,And concentrate the filtrate under reduced pressure,Purification by silica gel column chromatography,tert-Butyl 2-oxopyrrolidine-1-carboxylate (215.5 g) was isolated.

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  • 12
  • [ 202925-92-6 ]
  • [ 85909-08-6 ]
YieldReaction ConditionsOperation in experiment
77% With sodium periodate; ruthenium(III) trichloride hydrate In tetrachloromethane; water; acetonitrile at 20℃; for 16 h; General procedure: To a solution of 7a-l (2 mmol) was stirred in CH3CN/CCl4/H2O (v/v=2:2:1) at room temperature, the NaIO4 (8 mmol) was added in one portion and stirred for 10 min. The RuCl3*H2O (catalytic amount, 5percent) was added in portion. After being stirred for overnight, the reaction was diluted with Et2O and stirred for 1 h. The mixture was filtered and separated. The aqueous layer was extracted with DCM for three times and the combined organic layers were washed with brine for three tomes. Dried over anhydrous Na2SO4, filtered, and concentrated, the residue was purified by chromatography on silica gel to give 1a-l.
Reference: [1] Tetrahedron, 2011, vol. 67, # 40, p. 7829 - 7837
  • 13
  • [ 75178-87-9 ]
  • [ 85909-08-6 ]
Reference: [1] Chemistry--A European Journal, 2012, vol. 18, # 37, p. 11524 - 11527,4
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  • [ 57294-38-9 ]
  • [ 85909-08-6 ]
Reference: [1] European Journal of Organic Chemistry, 2007, # 20, p. 3380 - 3391
[2] Heterocycles, 1992, vol. 33, # 1, p. 131 - 134
  • 15
  • [ 86953-79-9 ]
  • [ 85909-08-6 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 30, p. 5541 - 5544
[2] RSC Advances, 2013, vol. 3, # 43, p. 19765 - 19768
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 15, p. 4078 - 4082[4] Angew. Chem., 2018, vol. 130, # 15, p. 4142 - 4146,5
  • 16
  • [ 616-45-5 ]
  • [ 34619-03-9 ]
  • [ 85909-08-6 ]
Reference: [1] Patent: US2009/82464, 2009, A1, . Location in patent: Page/Page column 37
  • 17
  • [ 1333-82-0 ]
  • [ 83220-73-9 ]
  • [ 85909-08-6 ]
Reference: [1] Patent: US2003/144267, 2003, A1,
  • 18
  • [ 85909-08-6 ]
  • [ 141293-14-3 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 52, p. 12252 - 12263
  • 19
  • [ 67-56-1 ]
  • [ 85909-08-6 ]
  • [ 144688-69-7 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With diisobutylaluminium hydride In diethyl ether; toluene at -78 - 20℃;
Stage #2: at 20℃; for 48 h;
[002081 step 2: fert-butyl 2-methoxypyrrolidine-l-carboxylate (51b). To a solution of 51a (20.0 g, 107.98 mmol) in dry Et20 (250 mL) cooled to -78°C was added portionwise 1M DIBAL-H solution in toluene (73.426 mL, 110.14 mmol). The mixture was stirred for 1 h at -78 °C, then allowed to warm to RT and stirred overnight. The reaction mixture was cooled to 0 °C, and saturated NH CI (50 mL) was added, followed by 1M Rochelle's Salt solution (300 mL). The mixture was transferred to a 2L Erlenmeyer flask, more ether was added, and it was stirred vigorously for 1 h (emulsion loosens and separates over this time). The mixture was transferred to a separatory funnel, the aqueous solution was drained, and the organics were washed with Rochelle's Salt solution and brine, dried (Na2S04), filtered, and concentrated. The resulting oil was then concentrated one time from MeOH. The resulting oil was dissolved in MeOH (250 mL) and p- TsOH monohydrate (1.0270 g, 5.3990 mmol) was added. The reaction mixture was stirred for 48 h at RT. The mixture was concentrated and the residue was taken up in DCM (300 mL), and this solution was poured into saturated NaHC03 (300 mL). The mixture was extracted with DCM, and the combined organic layers were dried (Na2S04), filtered, and concentrated to afford 20.09 g (92percent) of Slb as an oil.
Reference: [1] Patent: WO2013/20062, 2013, A1, . Location in patent: Paragraph 00208
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[3] Patent: WO2009/6567, 2009, A2, . Location in patent: Page/Page column 48-49
[4] Patent: WO2009/89352, 2009, A1, . Location in patent: Page/Page column 48
[5] Patent: WO2009/89359, 2009, A1, . Location in patent: Page/Page column 45-46
  • 20
  • [ 85909-08-6 ]
  • [ 144688-69-7 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 44, p. 7963 - 7966
[2] Tetrahedron Letters, 1994, vol. 35, # 23, p. 4019 - 4022
[3] Journal of Agricultural and Food Chemistry, 2014, vol. 62, # 6, p. 1233 - 1239
  • 21
  • [ 541-41-3 ]
  • [ 85909-08-6 ]
  • [ 188528-95-2 ]
YieldReaction ConditionsOperation in experiment
29.15% With lithium hexamethyldisilazane In tetrahydrofuran at -70℃; for 0.5 h; Inert atmosphere To THF (300 mL) is added LiHMDS (1.0 M, 6.80 L) at -70 under N2. Ethyl carbonochloridate (597.62 g, 5.51 mol) and tert-butyl 2-oxopyrrolidine-1-carboxylate (600.00 g, 3.24 mol) are added to the mixture at the same temperature and the mixture is stirred at -70 for 30 minutes. The reaction mixture is poured into an ice cold saturated solution of NH4Cl (1500 mL) and is separated. The aqueous layer is extracted with EtOAc (2×300 mL) and the combined organic extracts are washed with water (2×400 mL) , brine (2×400 mL) , dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue is slurried with MTBE (500 mL) at 15 for 20 minutes and filtered. The filter cake is washed with MTBE (2×100 mL) and dried in vacuum to give the title compound (270.00 g, 944.50 mmol, 29.15) as a white solid.1H NMR (CDCl3) δ 1.32 (t, 3H) , 1.54 (s, 9H) , 2.25 (m, 1H) , 2.39 (m, 1H) , 3.54 (m, 1H) , 3.72 (m, 1H) , 3.90 (m, 1H) , 4.25 (q, 2H) .
Reference: [1] Patent: WO2017/5069, 2017, A1, . Location in patent: Page/Page column 9
  • 22
  • [ 85909-08-6 ]
  • [ 79-22-1 ]
  • [ 431079-79-7 ]
YieldReaction ConditionsOperation in experiment
63%
Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5 h; Inert atmosphere
Stage #2: at -78℃; for 1 h; Inert atmosphere
To a solution of 1-(tert-butoxycarbonyl)-2-pyrrolidinone (2.3 g, 12.4 mmol) in tetrahydrofuran (100 ml) was added lithium bis(trimethylsilyl)amide (1.0 M in THF, 16.1 ml, 16.14 mmol) at -78 oC dropwise under nitrogen. The reaction was stirred at -78 oC for 30 min. To the above solution was added methyl chloroformate (1.72 ml, 22.22 mmol) dropwise. The mixture was stirred at -78 oC for 1 h, quenched with saturated ammonium chloride solution (40 ml), and extracted with ethyl acetate (100 ml x 3). The combined organic phase was washed with brine (100 ml x 2), dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography (eluting 0-30percent ethyl acetate in petroleum ether) to afford 1-tert-butyl 3-methyl 2-oxopyrrolidine-1,3-dicarboxylate (1.9 g, 63percent). 1H NMR (400 MHz, CDCl3) δ 3.89 - 3.78 (m, 1H), 3.74 (s, 3H), 3.72 - 3.69 (m, 1H), 3.56 - 3.53 (m, 1H), 2.41 - 2.37 (m, 1H), 2.26 - 2.21 (m, 1H), 1.53 (s, 9H).
45%
Stage #1: With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at 0 - 20℃;
Example 39 - Preparation of Intermediate 10 The synthesis of Intermediate 10 followed the procedure of General Procedure 9 following: Intermediate 10 To a cooled solution (-78oC) of diisopropylamine (8.74 g, 86.4 mmol, 1.6 eq) in anhydrous THF (200 mL) was added n-BuLi (34.5 mL, 86.4 mmol, 1.6 eq), followed by stirring at 0oC for 1 hour. The mixture was re-cooled to -78oC and to it was added tert-butyl-2-oxopyrrolidine-1-carboxylate (10.0 g, 54 mmol, 1.0 eq) portionwise, stirred for 1 hour and to it added methyl chloroformate (6.12 g, 64.8 mmol, 1.2 eq). The reaction mixture was allowed to come at room temperature and stirred overnight. It was monitored by TLC and LC-MS. After completion, the reaction mixture was quenched with ammonium chloride and evaporated to a residue, which was extracted with ethyl acetate (2 x 150 mL). The combined organic phases were washed with water, brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography using silica gel (60-120 mesh) eluting with 40percent ethyl acetate in n-hexane to give 1-(tert-butyl) 3- methyl 2-oxopyrrolidine-1,3-dicarboxylate (Intermediate 10, 9.46 g, yield: 45percent) m/z 188.17 [M-56]+; 1H NMR (400 MHz, CDCl3) δ 3.90 (ddd, J = 10.8, 8.5, 5.4 Hz, 1H), 3.81 (s, 3H), 3.73 (ddd, J = 10.8, 8.1, 6.6 Hz, 1H), 3.62– 3.52 (m, 1H), 2.50– 2.34 (m, 1H), 2.25 (dddd, J = 13.3, 9.1, 8.1, 5.4 Hz, 1H), 1.55 (s, 9H) ppm.
Reference: [1] Organic Letters, 2010, vol. 12, # 6, p. 1252 - 1254
[2] Tetrahedron, 2010, vol. 66, # 33, p. 6399 - 6410
[3] Tetrahedron Letters, 2002, vol. 43, # 6, p. 947 - 950
[4] Patent: WO2017/108723, 2017, A2, . Location in patent: Page/Page column 764; 765
[5] Patent: WO2016/138532, 2016, A1, . Location in patent: Paragraph 0274
  • 23
  • [ 85909-08-6 ]
  • [ 1319716-42-1 ]
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 32, p. 4204 - 4206
[2] Tetrahedron Letters, 2011, vol. 52, # 32, p. 4204 - 4206
[3] Patent: WO2015/94803, 2015, A1,
[4] Patent: WO2016/190847, 2016, A1,
[5] Patent: CN104974163, 2017, B,
[6] Patent: CN104672250, 2017, B,
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