1-((benzyloxy)carbonyl)-3-fluoropyrrolidine-3-carboxylic acid synthesis
- Product Name:1-((benzyloxy)carbonyl)-3-fluoropyrrolidine-3-carboxylic acid
- CAS Number:1432680-43-7
- Molecular formula:C13H14FNO4
- Molecular Weight:267.25
1228634-93-2
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Yield:1432680-43-7 73%
Reaction Conditions:
with triethylamine in tetrahydrofuran at 20; for 5 h;Inert atmosphere;Cooling with ice;
Steps:
4.3. 1-[(Benzyloxy)carbonyl]-3-fluoropyrrolidine-3-carboxylicacid (10)
Triethylamine (8.70 g, 0.086 mol, 2.3 equiv) and a solution of benzyl chloroformate (7.1 g, 0.041 mol, 1.1 equiv) in THF (25 mL)were consequentially added dropwise to an ice-cold suspension of7 (5.0 g, 0.037 mol,1 equiv) in anhydrous THF (75 mL). The obtainedmixture was stirred for 5 h at room temperature. Then the reactionmixture was diluted with saturated solution of NaHCO3 (100 mL)and extracted with EtOAc (350 mL). The organic phase waswashed with water (50 mL) and saturated solution of NaCl(350 mL), then separated and dried over anhydrous Na2SO4. Afterthat, the solvent was removed under reduced pressure to afford thepure compound 10 (7.30 g, 0.027 mol, 73% yield) as a yellow solid.Mp99e100 .1H NMR (500 MHz; CDCl3, Me4Si; 2 conformers are present) d:2.36e2.56 (m, 2H), 3.64 (m, 1H), 3.81e3.98 (m, 3H), 5.17 (s, 2H,CH2O), 7.27e7.37 (m, 5H, Ph), 8.45 (br s, 1H, OH).13C NMR (125 MHz; CDCl3; Me4Si; 2 conformers are present), d:35.3 (dd, 1J89 Hz, 2J23 Hz), 44.7 (d, J39 Hz), 55.1 (q, J27 Hz)67.7 (s, CH2O), 98.2 (q, JCF100 Hz), 128.0 (s, C6H5), 128.3 (s, C6H5),128.6 (s, C6H5), 136.0 (s, C6H5), 154.9 (2s, OCOBn), 171.7 (m, COOH).19F NMR (477 MHz; CDCl3; C6F6; 2 conformers are present) d:159.5 (159) (2m).Anal. Calcd for C13H14FNO4: C, 58.42; H, 5.28; N, 5.24. Found: C,58.54; H, 5.33; N, 5.38.LC-MS: 266 (M1).
References:
Yarmolchuk, Vladimir S.;Mykhalchuk, Vladimir L.;Mykhailiuk, Pavel K. [Tetrahedron,2014,vol. 70,# 18,p. 3011 - 3017]
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