Benzaldehyde → 2-[3-(1-Benzylpiperidin-4-ylidene)prop-1-ynyl]-6-methylpyridine

HRID 1895959ノート

反応式

HRID 1895959 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[N:3]=1.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(Cl)Cl>O>[CH2:17]([N:14]1[CH2:13][CH2:12][C:11](=[CH:10][C:9]#[C:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[N:3]=2)[CH2:16][CH2:15]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 240BenzaldehydeHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

生成物 1

HCID 875507132-[3-(1-Benzylpiperidin-4-ylidene)prop-1-ynyl]-6-methylpyridine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of the compound of Example 3 (0.22 g, 1.04 mmol), benzaldehyde (0.13 mL, 1.25 mmol), sodium triacetoxyborohydride (0.33 g, 1.56 mmol) and 15 mL of CH2Cl2 was stirred overnight at r.t. Afterwards, it was diluted with water, the organic layer was separated, washed with brine (2×15 mL), dried (Na2SO4) and evaporated to dryness in vacuo the give a crude, which was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with a gradient Petroleum Ether-EtOAc from 85:15 to 0:100 affording the title compound, which was further purified by preparative RP LC-MS chromatography, using MS-C18 XTerra column 30×50 mm eluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient (0.12 g).

後処理

  1. customthe organic layer was separated
  2. washwashed with brine (2×15 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness in vacuo the
  5. customgive a crude, which
  6. customwas purified by automated flash liquid chromatography (Horizon™-Biotage)
  7. washeluting with a gradient Petroleum Ether-EtOAc from 85:15 to 0:100 affording the title compound, which
  8. customwas further purified by preparative RP LC-MS chromatography
  9. washeluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient (0.12 g)

出典と根拠

ORDレコード
ord-901dddb84a7b4df59e8fc54be1a54a92
出典データセット
uspto-grants-2013_08
特許番号
US08518916B2

反応ノート

読み込み中…