(+-)-3-Quinuclidinol → Benzyl 4-[5-(1-azabicyclo[2.2.2]oct-3-yloxy)pyrazin-2-yl]phenylcarbamate

HRID 969988

反応式

HRID 969988 の反応式
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.O[C:11]1[N:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:19][CH:18]=2)=[N:15][CH:16]=1>>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:11]1[N:12]=[CH:13][C:14]([C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[CH:21][CH:22]=3)=[N:15][CH:16]=1)[CH2:2]2

参加物

3

反応物 2

HCID 15381(+-)-3-QuinuclidinolHCID 178521889HCID 178521889、化合物

生成物 1

HCID 69434813Benzyl 4-[5-(1-azabicyclo[2.2.2]oct-3-yloxy)pyrazin-2-yl]phenylcarbamate

実験手順

3-Quinuclidinol (Aldrich, 610 mg, 4.8 mmol) was treated with benzyl 4-(5-hydroxypyrazin-2-yl)phenylcarbamate (Ref. EP146282, 1.28 g, 4 mmol) according to the procedure of Example 5A. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3H2O, 90:10:1, Rf. 0.30) as solid (0.68 g, yield, 40%). 1H NMR (MeOH-d4, 300 MHz) δ 1.47-1.62 (m, 1H), 1.65-1.92 (m, 2H), 1.97-2.14 (m, 1H), 2.22-2.28 (m, 1H), 2.74-3.05 (m, 5H), 3.33-3.46 (m, 1H), 5.10-5.18 (m, 1H), 5.20 (s, 2H), 7.30-7.46 (m, 5H), 7.56 (d, J=8.8 Hz, 2H), 7.88 (d, J=8.8 Hz, 2H), 8.24 (d, J=1.4 Hz, 1H), 8.55 (d, J=1.4 Hz, 1H) ppm. MS (DCl/NH3) m/z 431 (M+H)+.

後処理

  1. customThe title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3H2O, 90:10:1, Rf. 0.30) as solid (0.68 g, yield, 40%)

出典と根拠

ORDレコード
ord-06aebaeae2844ee181cc615e5697a87e
出典データセット
uspto-grants-2007_12
特許番号
US07309699B2

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