Reaktion #9047

Reaktionsgleichung

sodium bicarbonate

(1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

methyl 4-formylbenzoate

NaBH(OAc)3

→

title compound

Ausbeute 74.0%

4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzoic acid methyl ester

Ausbeute 74.0%

Lösungsmittel

TFA

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred 3 h
2. 2
   Extraktionthe resulting mixture was extracted with CH2Cl2 (3×20 mL)
3. 3
   Trocknenthe combined organic extracts were dried (MgSO4)
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigePurification of the crude material by flash chromatography (silica gel, 50:2:1 CH2Cl2/MeOH/NH4OH)

Vorschrift

Following General Procedure B: To a solution of (1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (680 mg, 1.8 mmol) and methyl 4-formylbenzoate (295 mg, 1.8 mmol) in CH2Cl2 (10 mL) was added NaBH(OAc)3 (763 mg, 3.6 mmol) and the mixture stirred for 18 h. The resulting crude material was taken up in neat TFA (2 mL) and stirred 3 h. Saturated aqueous sodium bicarbonate (10 mL) was cautiously added, and the resulting mixture was extracted with CH2Cl2 (3×20 mL), and the combined organic extracts were dried (MgSO4), and concentrated in vacuo. Purification of the crude material by flash chromatography (silica gel, 50:2:1 CH2Cl2/MeOH/NH4OH) afforded the title compound (565 mg, 74%) as a white solid. 1H NMR (CDCl3) δ 1.64–1.75 (m, 1H), 2.01–2.08 (m, 2H), 2.26–2.28 (m, 1H), 2.74–2.76 (m, 1H), 2.81–2.86 (m, 1H), 3.81 (s, 2H), 3.86 (s, 3H), 3.94 (d, 1H, J=17 Hz), 4.09 (dd, 1H, J=9, 7 Hz), 4.21 (d, 1H, J=17 Hz), 7.18–7.22 (m, 3H), 7.44 (br d, 1H, J=8 Hz), 7.49 (d, 2H, J=8 Hz), 7.50–7.53 (m, 1H), 7.64–7.66 (m, 1H), 7.91 (d, 2H, J=8 Hz), 8.70 (dd, 1H, J=5, 1 Hz); 13C NMR (CDCl3) δ 21.2, 23.6, 29.0, 48.7, 51.9, 53.7, 111.0, 118.6, 121.5, 122.3, 129.3, 128.9, 129.5, 134.7, 137.2, 144.8, 146.8, 155.7, 157.1, 166.8. ES-MS m/z 427 (M+H). Anal. Calcd. for C26H26N4O2.0.6H2O.0.3CH2Cl2: C, 68.26; H, 6.05; N, 12.11. Found: C, 68.57; H, 6.12; N, 11.75.

Quelle