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Lithium borohydride → [3-Amino-4-(3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2':6',2'']terpyridin-1'-ylmethyl)-phenyl]-methanol

HRID 1987358
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1987358
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH:16]([C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:15][CH2:14][CH2:13][CH:12]2[C:24]2[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][N:25]=2)=[C:6]([NH2:31])[CH:5]=1.[Li+].[BH4-]>C1COCC1.[OH-].[Na+]>[NH2:31][C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][C:7]=1[CH2:10][N:11]1[CH:12]([C:24]2[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][N:25]=2)[CH2:13][CH2:14][CH2:15][CH:16]1[C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=1
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Komponenten

5

Edukt 2

HCID 4148881Lithium borohydrideHCID 674211763-amino-4-(3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2'; 6',2'']terpyridin-1'-ylmethyl)-benzoic acid methyl ester

Produkt 1

HCID 67421957[3-Amino-4-(3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2':6',2'']terpyridin-1'-ylmethyl)-phenyl]-methanolAusbeute 38,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel
HCID 14798
Sodium Hydroxide
Lösungsmittel

Versuchsvorschrift

To a solution of 3-amino-4-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-benzoic acid methyl ester (0.61 g, 1.42 mmol) in THF (14 mL) was added LiBH4 (430 mg, 19.74 mmol) and the mixture was heated to reflux overnight. The mixture was cooled to room temperature, diluted with 1.0 N NaOH (20 mL) and extracted with CH2Cl2 (5×30 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography on silica gel (2 mm plate, 20:1:1 CH2Cl2—CH3OH—NH4OH) provided 0.220 g (37%) of COMPOUND 59 as a white solid. 1H NMR (CDCl3) δ 1.23 (br s, 1H), 1.47-1.72 (m, 3H), 1.88-1.95 (m, 1H), 2.04-2.18 (m, 2H), 2.35 (s, 6H), 3.32 (s, 2H), 3.73 (dd, 2H, J=11.7, 3.0 Hz), 4.26 (d, 2H, J=3.3 Hz), 4.53 (br s, 2H), 6.03 (s, 1H), 6.07 (d, 1H, J=7.8 Hz), 6.48 (d, 1H, J=7.2 Hz), 6.86 (dd, 2H, J=7.8, 4.8 Hz), 7.15 (d, 2H, J=7.5 Hz), 8.33 (d, 2H, J=3.9 Hz). 13C NMR (CDCl3) δ 19.44, 25.02, 32.92, 60.69, 65.60, 68.25, 112.98, 115.09, 122.09, 122.80, 129.96, 131.38, 138.18, 140.42, 146.89, 147.51, 161.18; ES-MS m/z 403 (M+H). Anal. Calcd. For C25H30N4O.1.0H2O: C, 71.40; H, 7.67; N, 13.32. Found: C, 71.31; H, 7.55; N, 13.22.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. extractionextracted with CH2Cl2 (5×30 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification of the crude material by radial chromatography on silica gel (2 mm plate, 20:1:1 CH2Cl2—CH3OH—NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-b227d6cd32f047fdbe9e84a267f5725a
Quelldatensatz
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07550484B2

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