[1-(2-aminoethyl)pyrrolidin-2-yl]methanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To [1-(2-aminoethyl)-pyrrolidin-2-yl-]methanol (1.63 g, 11.3 mmol) in pyridine (10 mL) was added 1-chloroanthraquinone (1.37 g, 5.646 mmol), and the mixture was stirred at 65° C. for 24 hours. Pyridine was removed in vacuo and the resulting mixture of oil and solid was dissolved in CH2Cl2 and washed with H2O (3×50 mL) to remove any unreacted amine. The separated organic layer was removed in vacuo and the crude product was chromatographed using CH2Cl2/CH3OH (97:3). The desired product was yielded as a red powder (0.21 g, 11%). M.p. 113-115° C.; δH(250 MHz; CDCl3); 1.75-2.0 (m, 4H), 2.25-2.35 (m, 1H), 2.6-2.8 (m, 2H), 3.15-3.3 (m, 2H), 3.35-3.55 (m, 4H), 3.75-3.85 (2×d, 1H), 7.0 (2×d, 1H), 7.45-7.6 (m, 2H), 7.65-7.8 (m, 2H), 8.2 (2×d, H), 8.45 (2×d), and 10.05 (s, 1H, C(1)NH); δC(62.9 MHz; CDCl3); 24.11, 27.15, 41.64, 52.99, 53.82, 62.61, 65.26, 113.15, 115.60, 126.57, 132.86, 133.81, 135.32, 151.49, 183.77, and 184.89; FAB MS, m/z(M+H)+ 351; Anal. calcd for C21H22N2O3: C, 71.98; H, 6.33; N, 8.00. Found: C, 71.79; H, 6.13; N, 8.07. Pyridine was removed in vacuo the resulting mixture of oil and solid was dissolved in CH2Cl2 washed with H2O (3×50 mL) to remove any unreacted amine The separated organic layer was removed in vacuo the crude product was chromatographed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The method follows that of S6 using 2-hydroxymethyl-pyrrolidin-1-yl-acetonitrile (19.5 g, 0.139 mol), LiAlH4 (15.84 g, 0.417 mol) and dry THF (150 mL). The title-compound (12.5 g, 63%) was afforded as straw-coloured oil by kugelrohr distillation (142° C., 0.3 mbar). δH (250 MHz; CDCl3); 1.6-1.9 (m, 4H, CH2CH2CH2, CH2CH2CH), 1.98 (s (broad), 3H, NH2, OH), 2.3 (m, 1H), 2.45 (m, 1H), 2.55 (m, 1H), 2.75-2.85 (m, 3H), 3.19 (m, 1H, NCHCH2), 3.4 (2×d, 1H, J=3 Hz and J=11 Hz, 1×CHCH2OH), 3.6 (2×d, 1H, J=3 Hz and J=11 Hz, 1×CHCH2OH); IR υmax/cm−1; 3375 (NH2), 3300 (NH2), 3200 (OH), 2970-2800 (CH2, CH3), 1600, 1475, 1375, 1230 and 1060; FAB MS, m/z(M+H)+ 145.

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To [1-(2-aminoethyl)-pyrrolidin-2-yl-]methanol (1.63 g, 11.3 mmol) in pyridine (10 mL) was added 1-chloroanthraquinone (1.37 g, 5.646 mmol), and the mixture was stirred at 65° C. for 24 hours. Pyridine was removed in vacuo and the resulting mixture of oil and solid was dissolved in CH2Cl2 and washed with H2O (3×50 mL) to remove any unreacted amine. The separated organic layer was removed in vacuo and the crude product was chromatographed using CH2Cl2/CH3OH (97:3). The desired product was yielded as a red powder (0.21 g, 11%). M.p. 113-115° C.; δH(250 MHz; CDCl3); 1.75-2.0 (m, 4H), 2.25-2.35 (m, 1H), 2.6-2.8 (m, 2H), 3.15-3.3 (m, 2H), 3.35-3.55 (m, 4H), 3.75-3.85 (2×d, 1H), 7.0 (2×d, 1H), 7.45-7.6 (m, 2H), 7.65-7.8 (m, 2H), 8.2 (2×d, H), 8.45 (2×d), and 10.05 (s, 1H, C(1)NH); δC(62.9 MHz; CDCl3); 24.11, 27.15, 41.64, 52.99, 53.82, 62.61, 65.26, 113.15, 115.60, 126.57, 132.86, 133.81, 135.32, 151.49, 183.77, and 184.89; FAB MS, m/z(M+H)+ 351; Anal. calcd for C21H22N2O3: C, 71.98; H, 6.33; N, 8.00. Found: C, 71.79; H, 6.13; N, 8.07. Pyridine was removed in vacuo the resulting mixture of oil and solid was dissolved in CH2Cl2 washed with H2O (3×50 mL) to remove any unreacted amine The separated organic layer was removed in vacuo the crude product was chromatographed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The method follows that of S6 using 2-hydroxymethyl-pyrrolidin-1-yl-acetonitrile (19.5 g, 0.139 mol), LiAlH4 (15.84 g, 0.417 mol) and dry THF (150 mL). The title-compound (12.5 g, 63%) was afforded as straw-coloured oil by kugelrohr distillation (142° C., 0.3 mbar). δH (250 MHz; CDCl3); 1.6-1.9 (m, 4H, CH2CH2CH2, CH2CH2CH), 1.98 (s (broad), 3H, NH2, OH), 2.3 (m, 1H), 2.45 (m, 1H), 2.55 (m, 1H), 2.75-2.85 (m, 3H), 3.19 (m, 1H, NCHCH2), 3.4 (2×d, 1H, J=3 Hz and J=11 Hz, 1×CHCH2OH), 3.6 (2×d, 1H, J=3 Hz and J=11 Hz, 1×CHCH2OH); IR υmax/cm−1; 3375 (NH2), 3300 (NH2), 3200 (OH), 2970-2800 (CH2, CH3), 1600, 1475, 1375, 1230 and 1060; FAB MS, m/z(M+H)+ 145.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To [1-(2-aminoethyl)-pyrrolidin-2-yl-]methanol (1.63 g, 11.3 mmol) in pyridine (10 mL) was added 1-chloroanthraquinone (1.37 g, 5.646 mmol), and the mixture was stirred at 65° C. for 24 hours. Pyridine was removed in vacuo and the resulting mixture of oil and solid was dissolved in CH2Cl2 and washed with H2O (3×50 mL) to remove any unreacted amine. The separated organic layer was removed in vacuo and the crude product was chromatographed using CH2Cl2/CH3OH (97:3). The desired product was yielded as a red powder (0.21 g, 11%). M.p. 113-115° C.; δH(250 MHz; CDCl3); 1.75-2.0 (m, 4H), 2.25-2.35 (m, 1H), 2.6-2.8 (m, 2H), 3.15-3.3 (m, 2H), 3.35-3.55 (m, 4H), 3.75-3.85 (2×d, 1H), 7.0 (2×d, 1H), 7.45-7.6 (m, 2H), 7.65-7.8 (m, 2H), 8.2 (2×d, H), 8.45 (2×d), and 10.05 (s, 1H, C(1)NH); δC(62.9 MHz; CDCl3); 24.11, 27.15, 41.64, 52.99, 53.82, 62.61, 65.26, 113.15, 115.60, 126.57, 132.86, 133.81, 135.32, 151.49, 183.77, and 184.89; FAB MS, m/z(M+H)+ 351; Anal. calcd for C21H22N2O3: C, 71.98; H, 6.33; N, 8.00. Found: C, 71.79; H, 6.13; N, 8.07. Pyridine was removed in vacuo the resulting mixture of oil and solid was dissolved in CH2Cl2 washed with H2O (3×50 mL) to remove any unreacted amine The separated organic layer was removed in vacuo the crude product was chromatographed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The method follows that of S6 using 2-hydroxymethyl-pyrrolidin-1-yl-acetonitrile (19.5 g, 0.139 mol), LiAlH4 (15.84 g, 0.417 mol) and dry THF (150 mL). The title-compound (12.5 g, 63%) was afforded as straw-coloured oil by kugelrohr distillation (142° C., 0.3 mbar). δH (250 MHz; CDCl3); 1.6-1.9 (m, 4H, CH2CH2CH2, CH2CH2CH), 1.98 (s (broad), 3H, NH2, OH), 2.3 (m, 1H), 2.45 (m, 1H), 2.55 (m, 1H), 2.75-2.85 (m, 3H), 3.19 (m, 1H, NCHCH2), 3.4 (2×d, 1H, J=3 Hz and J=11 Hz, 1×CHCH2OH), 3.6 (2×d, 1H, J=3 Hz and J=11 Hz, 1×CHCH2OH); IR υmax/cm−1; 3375 (NH2), 3300 (NH2), 3200 (OH), 2970-2800 (CH2, CH3), 1600, 1475, 1375, 1230 and 1060; FAB MS, m/z(M+H)+ 145.