7-[(E)-2-(6-methylpyridin-3-yl)vinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole → 7-[2-(6-methylpyridin-3-yl)ethyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

HRID 37787ノート

反応式

HRID 37787 の反応式
[CH3:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[C:18]3[NH:17][C:16]4[CH:19]5[CH2:25][CH2:24][N:22]([CH2:23][C:15]=4[C:14]=3[CH:13]=[CH:12][CH:11]=2)[CH2:21][CH2:20]5)=[CH:4][CH:3]=1>O=[Pt]=O.C(O)C>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[C:18]3[NH:17][C:16]4[CH:19]5[CH2:25][CH2:24][N:22]([CH2:23][C:15]=4[C:14]=3[CH:13]=[CH:12][CH:11]=2)[CH2:21][CH2:20]5)=[CH:4][CH:3]=1

参加物

4

反応物 1

HCID 532507617-[(E)-2-(6-methylpyridin-3-yl)vinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

生成物 1

HCID 532507627-[2-(6-methylpyridin-3-yl)ethyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 702Ethanol溶媒

実験手順

Adam's catalyst (PtO2, 7 mg, 0.031 mmol; Aldrich) was added to a solution of the product of Example 1D (60 mg, 0.18 mmol) in ethanol (5 mL). The reaction flask was evacuated and purged with nitrogen (3 cycles) then evacuated and purged with hydrogen (4 cycles), and the mixture was stirred under hydrogen (1 atm) at room temperature for 18 hours. The flask was evacuated and purged with nitrogen (3 cycles), and the reaction mixture was filtered. The filtrate was concentrated under vacuum, and the residue was purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 35-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (500 MHz, methanol-d4) δ ppm 2.06 (td, J=7.3, 3.7 Hz, 4 H), 2.45 (s, 3 H), 2.99 (t, J=7.6 Hz, 2 H), 3.01-3.09 (m, 3 H), 3.11 (t, J=7.6 Hz, 2 H), 3.23 (dq, J=7.3, 7.1 Hz, 2 H), 4.20 (s, 2 H), 6.77 (d, J=7.0 Hz, 1 H), 6.88 (t, J=7.5 Hz, 1 H), 7.13 (d, J=7.6 Hz, 1 H), 7.14 (d, J=7.9 Hz, 1 H), 7.49 (dd, J=7.9, 2.1 Hz, 1 H), 8.11 (d, J=1.8 Hz, 1 H); MS (APCI) m/z 332 (M+H)+.

後処理

  1. customThe reaction flask was evacuated
  2. custompurged with nitrogen (3 cycles)
  3. customthen evacuated
  4. custompurged with hydrogen (4 cycles)
  5. customThe flask was evacuated
  6. custompurged with nitrogen (3 cycles)
  7. filtrationthe reaction mixture was filtered
  8. concentrationThe filtrate was concentrated under vacuum
  9. customthe residue was purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 35-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)]

出典と根拠

ORDレコード
ord-faf67b9a1465450a949668a0c2fabe32
出典データセット
uspto-grants-2013_09
特許番号
US08524703B2

反応ノート

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