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

HRID 1483957노트

반응식

HRID 1483957 반응식
[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]

참가 물질

5

반응물 2

HCID 86714289(R)-2-((1-butyrylpiperidin-2-yl)methoxy)-6-nitrobenzonitrileHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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+).

후처리

  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%)

출처 및 근거

ORD 기록
ord-7603722a443a481ba7e647cba3d840c6
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09420814B2

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