trans‐2,5‐Dimethylpyrrolidine

(racemate) [62617-69-0; 39713-72-9] C6H13N (MW 99.18) InChI = 1S/C6H13N/c1-5-3-4-6(2)7-5/h5-7H,3-4H2,1-2H3 InChIKey = ZEBFPAXSQXIPNF-UHFFFAOYSA-N InChI = 1/C6H13N/c1-5-3-4-6(2)7-5/h5-7H,3-4H2,1-2H3 InChIKey = ZEBFPAXSQXIPNF-UHFFFAOYAQ (2S,5S) [117968-50-0] (MW 135.64) InChI = 1S/C6H13N/c1-5-3-4-6(2)7-5/h5-7H,3-4H2,1-2H3/t5-,6-/m0/s1 InChIKey = ZEBFPAXSQXIPNF-WDSKDSINSA-N (2R,5R) [62617-70-3] InChI = 1S/C6H13N/c1-5-3-4-6(2)7-5/h5-7H,3-4H2,1-2H3/t5-,6-/m1/s1 InChIKey = ZEBFPAXSQXIPNF-PHDIDXHHSA-N (·HCl, racemate) [114143-75-8; 4832-49-9] C6H14ClN InChI = 1/C6H13N.ClH/c1-5-3-4-6(2)7-5;/h5-7H,3-4H2,1-2H3;1H/fC6H14N.Cl/h7H;1h/q+1;-1 InChIKey = AFHNFHHYTYQLIO-JSSCSLHPCN InChI = 1/C6H13N.ClH/c1-5-3-4-6(2)7-5;/h5-7H,3-4H2,1-2H3;1H/fC6H14N.Cl/h7H;1h/q+1;-1 InChIKey = AFHNFHHYTYQLIO-JSSCSLHPCN (·HCl, 2S,5S) [138133-34-3] InChI = 1S/C6H13N.ClH/c1-5-3-4-6(2)7-5;/h5-7H,3-4H2,1-2H3;1H/t5-,6-;/m0./s1 InChIKey = AFHNFHHYTYQLIO-GEMLJDPKSA-N (·HCl, 2R,5R) [70144-18-2] InChI = 1S/C6H13N.ClH/c1-5-3-4-6(2)7-5;/h5-7H,3-4H2,1-2H3;1H/t5-,6-;/m1./s1 InChIKey = AFHNFHHYTYQLIO-KGZKBUQUSA-N (C2 symmetric chiral pyrrolidine,1 useful in optically active form as a chiral auxiliary in a variety of asymmetric reactions) Physical Data: free amine: bp 102–103 °C; (2S,5S) [α]D25 +10.6° (c 1.0, EtOH);2 (2R,5R) [α]D25 −11.5° (c 1.0, EtOH).2 Hydrochloride: racemate mp 187–189 °C;3 (2S,5S) mp 200–201 °C,4 [α]D25 −5.63° (c 0.67, CH2Cl2);4 (2R,5R) mp 200–203 °C,5 [α]D25 +5.57° (c 1.18, CH2Cl2).5 Form Supplied in: colorless oil; commercially available as a mixture of (±)-trans and cis isomers (the mixture is not easily separated).6 Purification: the free amine can be purified by fractional distillation; the hydrochloride salt can be recrystallized from absolute ethanol and diethyl ether. Handling, Storage, and Precautions: irritant; flammable. Use in a fume hood.