(R)-2-((1-butyrylpiperidin-2-yl)methoxy)-6-nitrobenzonitrile → (R)-2-amino-6-((1-butyrylpiperidin-2-yl)methoxy)benzonitrile

HRID 1483957ノート

反応式

HRID 1483957 の反応式
[C:1]([N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]1[CH2:12][O:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[C:15]=1[C:16]#[N:17])(=[O:5])[CH2:2][CH2:3][CH3:4].[H][H]>C(O)C.[Pd]>[NH2:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:14]([O:13][CH2:12][C@H:7]2[CH2:8][CH2:9][CH2:10][CH2:11][N:6]2[C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[C:15]=1[C:16]#[N:17]

参加物

5

反応物 2

HCID 86714289(R)-2-((1-butyrylpiperidin-2-yl)methoxy)-6-nitrobenzonitrileHCID 178418361HCID 178418361、化合物

生成物 1

HCID 86714288(R)-2-amino-6-((1-butyrylpiperidin-2-yl)methoxy)benzonitrile収率 81%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

To a solution of (R)-2-((1-butyrylpiperidin-2-yl)methoxy)-6-nitrobenzonitrile (Example 16b, 1.5 g, 4.53 mmol) in ethanol (40 mL) was added 10% Pd/C (300 mg). The reaction mixture was charged with hydrogen balloon at room temperature overnight then then filtered through celite and concentrated under reduced pressure. The residue was purified by Biotage SP-1 (40s column) eluting with EtOAc/Hexane (10%-70%) to give the desired product as an oil (1.1 g, 81%). H NMR (400 MHz, DMSO-d6) δ 0.86 (t, J=7.2 Hz, 3H), 1.46-1.65 (m, 7H), 1.77-1.85 (m, 1H), 2.24-2.30 (m, 1H), 2.38-2.42 (m, 1H), 2.56-2.63 (m, 0.5H), 3.1-3.16 (m, 0.5H), 3.71-3.74 (m, 0.3H), 3.92-3.98 (m, 1H), y 2H), 7.15-7.19 (m, 1H). MS 302 (MH+).

後処理

  1. filtrationfiltered through celite and
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by Biotage SP-1 (40s column)
  4. washeluting with EtOAc/Hexane (10%-70%)

出典と根拠

ORDレコード
ord-7603722a443a481ba7e647cba3d840c6
出典データセット
uspto-grants-2016_08
特許番号
US09420814B2

反応ノート

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