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

HRID 1618950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1618950
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

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]+.

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-6b1654a069b14753a5b7ae420d793e40
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772286B2

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