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With potassium tert-butylate; In toluene; for 2h;Cooling with ice;
The crude 1127.324 g compound (c) is dissolved in 2.5 L toluene without water, 243.028g tert potassium butanolate is added gradually under ice bath, stirred for 2h, TLC was carried out to detect the completion of the reaction, 4M HCl in ice bath was added, PH in acidic was adjusted to PH=8 using saturated sodium bicarbonate, extracted with ethyl acetate, dried using anhydrous Na2SO4, filtered, and spin-dried to obtain 376.7g pink solid compound (d), yield 98percent.
78%
With potassium tert-butylate; In toluene; at 0℃; for 2h;
Above-prepared ethyl 3-[N-benzyl-N-(ethoxycarbonylmethyl)amino]propionate (14.0 g, 0.0479 mol) was dissolved in toluene (100 mL), and the solution was mixed with potassium tert-butoxide (5.9 g, 0.0525 mol) gradually added under ice-cooling, followed by stirring under ice-cooling for two hours. The reaction mixture was mixed with diluted hydrochloric acid (about 1 mol/L, 100 mL) under ice-cooling, followed by shaking and separation, to yield an aqueous layer. Saturated aqueous sodium bicarbonate solution (300 mL) was added dropwise to the aqueous layer, and ethyl acetate (400 mL) was further added thereto, followed by shaking and separation. After drying the organic layer over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, to thereby yield ethyl 1-benzyl-4-oxopyrrolidine-3-carboxylate (9.23 g, in a yield of 78percent).
By following the same procedure but using the corresponding ethyl N,N-disubstituted-glycinates the following 1-substituted 4-ethoxycarbonylpyrrolidine-3-ones are synthesised....4-ethoxycarbonyl-1-(3,4,5-trichlorophenyl)pyrrolidine-3-one,4-ethoxycarbonyl-1-(2,4,6-tribromophenyl)pyrrolidine-3-one,4-ethoxycarbonyl-1-(2,4,5-tribromophenyl)pyrrolidine-3-one,4-ethoxycarbonyl-1-(3,4,5-tribromophenyl)pyrrolidine-3-one,4-ethoxycarbonyl-1-benzylpyrrolidine-3-one,4-ethoxycarbonyl-1-(2-methoxybenzyl)pyrrolidine-3-one,4-ethoxycarbonyl-1-(3-methoxybenzyl)pyrrolidine-3-one,4-ethoxycarbonyl-1-(4-methoxybenzyl)pyrrolidine-3-one,...
5
[ 1027-35-6 ]
[ 780-15-4 ]
Yield
Reaction Conditions
Operation in experiment
With sodium tetrahydroborate; In methanol; ethyl acetate;
Preparation of 1-Benzyl-4-hydroxymethyl-pyrrolidin-3-ol (I-4c): Intermediate I-4b (0.0162 mol, 4.0 g, 1eq) was dissolved in 60 mL of MeOH and the cooled to 0° C. NaBH4 (0.0971, 3.67 g, 6 eq) was added in 250 mg portions over an hour period. The mixture was warmed to room temperature and allowed to stir overnight. The MeOH was removed in vacuo and the residue was taken up in EtOAc (60 mL) and 2N NaOH (20 mL). The mixture was shaken for approximately 2 to 3 minutes in a separation funnel. The organic phase was separated and the aqueous phase was washed with 2*50 mL more EtOAc. The organic layers were combined, dried over sodium sulfate and concentrated in vacuo to a pale yellow oil which was placed under high vacuum for 2 hours to afford a clear pale yellow gum 2.06 g (65percent).
1.88 g
With methanol; sodium tetrahydroborate; at 0 - 20℃;
To a stirred solution of <strong>[1027-35-6]ethyl 1-benzyl-4-oxopyrrolidine-3-carboxylate</strong> (5 g, 20.2 mmol)in MeOH (75 mL) at 0 °C, NaBH4 (4.58 g, 121.2 mmol) was added in portion of 250 mg over30?. Then the solution was warmed to RT and stirred ON. Solvent was removed under vacuum. The residue was dissolved in EtOAc (75 mL) and NaOH 2 M (25 mL), organic phase was separated and the aqueous phase was washed again with EtOAc (60 mL x2). Combined organics were dried over Na2504 and concentrated to obtain 5.7 g of a yellow oil that was purified by FCon 5i02 cartridge (eluting from DCM to MeOH 100percent) to obtain 1.88 g of title compound as yellow oil (p133). MS (m/z):208.2 [IVll{]t
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