5,6,7,8-Tetrahydro-1,8-naphthyridine-2-carbaldehyde → (5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)methanol

HRID 585569ノート

反応式

HRID 585569 の反応式
[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:11]=[O:12]>C1COCC1>[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][OH:12]

参加物

3

反応物 1

HCID 218737255,6,7,8-Tetrahydro-1,8-naphthyridine-2-carbaldehyde

生成物 1

HCID 22337336(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)methanol収率 59.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
5 °C

実験手順

A mixture of 5,6,7,8-tetrahydro-[1,8]naphthyridine-2-carboxaldehyde 1 (0.5 g) and lithhiumborohydride (3.0 mL, 2.0 M) in THF (5.0 ML) was stirred at 5° C. for 1 h. The reaction mixture was then allowed to warm to room temperature over a period of another hour, quenched with acetic acid (2.0 mL) and concentrated under reduced pressure. The residue was partitioned between 1N NaOH (20.0 mL)and EtOAc (25 mL). The organic phase was washed with brine (2×0 mL), dried (Na2SO4), and concentrated to dryness. The resulting residue was purified by silica gel flash chromatography using EtOAc containing 10% methanol to give 0.3 g of the title compound as a pale yellow solid: 1H-NMR δ (CD3OD) 7.18 (d, 1H, J=7.6 Hz), 6.58 (d, 1H, J=7.6 Hz), 4.40 (s, 2H), 3.34 (m, 2H), 2.69 (t, 2H, J=6.0 Hz), 1.85 (t, 2H, J=6.0 Hz); ES-MS, m/z =165 (MH+).

後処理

  1. temperatureto warm to room temperature over a period of another hour
  2. customquenched with acetic acid (2.0 mL)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between 1N NaOH (20.0 mL)and EtOAc (25 mL)
  5. washThe organic phase was washed with brine (2×0 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to dryness
  8. customThe resulting residue was purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-7a7d17e538b1412f8b8c16af5d934d6c
出典データセット
uspto-grants-2005_08
特許番号
US06933304B2

反応ノート

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