Reaktion #1056541

Reaktionsgleichung

(S)-4-(3-Iodo-2-methylpropyl]-4H-benzo[1,4]thiazin-3-one

3-pentyl-8-azabicyclo[3.2.1]octane

→

title compound ( 108LM52-49 )

Ausbeute 49.0%

(R)-4-[2-Methyl-3-(3-pentyl-8-aza-bicyclo[3.2.1]oct-8-yl)propyl]-4H-benzo[1,4]thiazin-3-one

Ausbeute 49.0%

Lösungsmittel

MeCN

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigePurified by cation exchange CC and flash CC (SiO2; MeOH/DCM 1:50+1% Et3N)

Vorschrift

The compound (S)-4-(3-Iodo-2-methylpropyl]-4H-benzo[1,4]thiazin-3-one (108LM37-34) (0.080 g, 0.231 mmol) and 3-pentyl-8-azabicyclo[3.2.1]octane (104KS32-2) (0.050 g, 0.276 mmol) in MeCN (½ mL) were reacted according to GP10 shaking at 40° C. for 5 days. Purified by cation exchange CC and flash CC (SiO2; MeOH/DCM 1:50+1% Et3N) to give the title compound (108LM52-49) (0.045 g, 49%). 1H NMR (CDCl3) δ 7.36 (d, J=7.6 Hz, 1H), 7.32 (d, J=7.7 Hz, 1H), 7.22 (t, J=7.6 Hz, 1H), 7.00 (t, J=7.6 Hz, 1H), 4.16 (d, J=7.3 Hz, CH2), 3.34 (s, CH2), 3.10-2.95 (m, 2H), 2.25-2.17 (m, 1H), 2.15-2.03 (m, 3H), 1.94-1.75 (m, 3H), 1.70-1.60 (m, 1H), 1.60-1.50 (m, 2H), 1.40-1.15 (m, 10H), 0.90-0.80 (m, 6H); 13C NMR (CDCl3) δ 166.1, 139.2, 128.7, 127.1, 124.7, 123.4, 119.1, 60.5, 59.0, 57.4, 47.5, 38.4, 36.4, 32.2, 32.1, 31.4, 29.9, 28.5, 28.4, 27.9, 27.2, 22.9, 16.7, 14.3; HPLC-MS (ammonium acetate) [M+H]+=401.3.

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