4-Methoxybenzaldehyde → 1-Tert-butyl 4-methyl 4-((4-methoxybenzylamino)methyl)piperidine-1,4-dicarboxylate

HRID 1618950노트

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HRID 1618950 반응식
[NH2:1][CH2:2][C:3]1([C:16]([O:18][CH3:19])=[O:17])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.C([BH3-])#N.[Na+]>CO>[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH:1][CH2:2][C:3]2([C:16]([O:18][CH3:19])=[O:17])[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])[CH2:7][CH2:8]2)=[CH:24][CH:23]=1

참가 물질

5

반응물 3

HCID 312444-MethoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 254188221-tert-Butyl 4-methyl 4-(aminomethyl)piperidine-1,4-dicarboxylate

생성물 1

HCID 683146401-Tert-butyl 4-methyl 4-((4-methoxybenzylamino)methyl)piperidine-1,4-dicarboxylate수율 58%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
45 °C

실험 절차

Commercial available 1-tert-butyl 4-methyl 4-(aminomethyl)piperidine-1,4-dicarboxylate (10.10 mmol, 2.75 g) and 4-methoxybenzaldehyde (15.15 mmol, 2.062 g) in anhydrous MeOH (40 mL) were stirred for 2 h at rt. After addition of sodium cyanoborohydride (20.19 mmol, 1.269 g) the reaction was stirred overnight at 45° C. The mixture was evaporated in vacuo, and solved in EtOAc and sat. aq. bicarb. After separation of the organic phase, the aq. phase was extracted with EtOAc. The combined organic phase was dried over MgSO4 and evaporated in vacuo. The crude was purified by flash chromatography (heptane/EtOAc: 10 to 100%) yielding 2.3 g oil (58%). 1H NMR (400 MHz, CDCl3, 300K): δ=1.40 (2H, s), 1.45 (9H, s), 2.07 (2H, dt, J=13.3 Hz, J=3.4 Hz), 2.66 (2H, m), 2.94 (2H, m), 3.68 (2H, s), 3.70 (3H, s), 3.76 (2H, m), 3.79 (3H, s), 6.85 (2H, d, J=8.3 Hz), 7.19 (2H, d, J=8.3 Hz). 13C NMR (100 MHz, CDCl3, 300K): δ=28.8, 31.9, 47.3, 52.3, 53.9, 55.7, 57.3, 79.8, 114.0, 129.4, 132.8, 155.2, 159.0, 176.1. MS (ES) C21H32N2O5 requires: 392. found: 393.3 [M+H]+.

후처리

  1. customThe mixture was evaporated in vacuo
  2. customAfter separation of the organic phase
  3. extractionthe aq. phase was extracted with EtOAc
  4. dry with materialThe combined organic phase was dried over MgSO4
  5. customevaporated in vacuo
  6. customThe crude was purified by flash chromatography (heptane/EtOAc: 10 to 100%)

출처 및 근거

ORD 기록
ord-6b1654a069b14753a5b7ae420d793e40
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772286B2

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