Reaktion #1056540

Reaktionsgleichung

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

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

3-butyl-8-aza-bicyclo[3.2.1]octane

→

title compound ( 108LM51-48 )

Ausbeute 40.4%

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

Ausbeute 40.4%

Lösungsmittel

MeCN

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigePurified by cation exchange CC and flash CC (SiO2; MeOH/DCM 1:10)

Vorschrift

The compound (S)-4-(3-Iodo-2-methyl-propyl)-4H-benzo[1,4]thiazin-3-one (108LM37-34) (0.093 g, 0.269 mmol) and 3-butyl-8-aza-bicyclo[3.2.1]octane (104KS29) (0.054 g, 0.323 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 1:10) to give the title compound (108LM51-48) (0.042 g, 40%). 1H NMR (CDCl3) δ 7.38 (d, J=7.8 Hz, 1H), 7.33 (d, J=8.1 Hz, 1H), 7.22 (t, J=7.9 Hz, 1H), 7.00 (t, J=8.0 Hz, 1H), 4.18-4.10 (m, 2H), 3.38 (s, CH2), 3.15-3.00 (m, 2H), 2.30-2.22 (mn, 1H), 2.20-2.10 (m, 1H), 1.90-1.75 (m, 3H), 1.60-1.40 (m, 5H), 1.40-1.15 (m, 8H), 0.90-0.82 (mn, 6H); 13C NMR (CDCl3) δ 166.1, 139.2, 128.7, 127.2, 124.7, 123.5, 119.1, 61.4, 60.1, 57.3, 47.6, 38.3, 36.9, 32.1, 31.2, 29.9, 29.4, 28.2, 27.2, 26.5, 23.1, 16.7, 14.3; HPLC-MS (ammonium acetate) [M+H]+=387.3.

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