Acetaldehyde → HCID 67979996, 화합물

HRID 1622310노트

반응식

HRID 1622310 반응식
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]

참가 물질

7

반응물 5

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5003444Sodium cyanoborohydrideHCID 67979956HCID 67979956, 화합물

생성물 1

HCID 67979996HCID 67979996, 화합물수율 22%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-47120239d9794948996d6b5b888f269a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778931B2

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