Acetaldehyde → HCID 67979996、化合物

HRID 1622310ノート

反応式

HRID 1622310 の反応式
C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]([N:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:27]([O:29][CH3:30])=[O:28])[CH:23]=3)[CH2:18]2)=[O:16])([CH3:14])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.[CH:32](=O)C.[O-]S([O-])(=O)=O.[Mg+2].C([BH3-])#N.[Na+]>CO>[CH2:6]([N:8]1[CH2:9][CH2:10][C:11]([C:15]([N:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:27]([O:29][CH3:30])=[O:28])[CH:23]=3)[CH2:18]2)=[O:16])([CH3:14])[CH2:12][CH2:13]1)[CH3:32]

参加物

7

反応物 5

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5003444Sodium cyanoborohydrideHCID 67979956HCID 67979956、化合物

生成物 1

HCID 67979996HCID 67979996、化合物収率 22%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of methyl 2-{[1-(tert-butoxycarbonyl)-4-methylpiperidin-4-yl]carbonyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate.[HCl] (0.260 g, 0.737 mmol) in MeOH (8.0 mL) was treated with acetaldehyde (0.414 g, 7.37 mmol) and MgSO4 (excess). The reaction mixture was stirred at rt for 1 h, and sodium cyanoborohydride (93 mg, 1.47 mmol) was added in portions. The resulting mixture was stirred for 3 h at rt and then filtered to remove the MgSO4. The filtrate was washed with water and brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by column chromatography (SiO2, 0-20% MeOH in DCM) to give methyl 2-[(1-ethyl-4-methylpiperidin-4-yl)carbonyl]-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (55 mg, 22%). LC-MS: (FA) ES+ 345; 1H NMR (400 MHz, CDCl3) δ 7.86-7.80 (m, 2H), 7.18 (d, J=7.9 Hz, 1H), 4.78 (s, 2H), 3.89 (s, 3H), 3.88-3.83 (m, 2H), 2.91 (t, J=5.5 Hz, 2H), 2.77-2.67 (m, 2H), 2.42 (q, J=7.2 Hz, 2H), 2.36-2.20 (m, 4H), 1.75-1.65 (m, 2H), 1.30 (s, 3H), 1.09 (t, J=7.2 Hz, 3H).

後処理

  1. stirringThe resulting mixture was stirred for 3 h at rt
  2. filtrationfiltered
  3. customto remove the MgSO4
  4. washThe filtrate was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by column chromatography (SiO2, 0-20% MeOH in DCM)

出典と根拠

ORDレコード
ord-47120239d9794948996d6b5b888f269a
出典データセット
uspto-grants-2014_07
特許番号
US08778931B2

反応ノート

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