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Aluminium lithium hydride → 2-(4-{[(3,5-Dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-3-hydroxymethyl-benzylamino)-ethanol

HRID 251277
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 251277
C[O:2][C:3](=O)[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]([CH2:25][C:26]2[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][N:27]=2)[CH:15]2[C:24]3[N:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:18][CH2:17][CH2:16]2)=[C:9]([CH2:34][OH:35])[CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH4+:5].[OH-:2].[CH3:32][C:31]1[C:26]([CH2:25][N:14]([CH2:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][NH:5][CH2:4][CH2:3][OH:2])=[CH:8][C:9]=2[CH2:34][OH:35])[CH:15]2[C:24]3[N:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:18][CH2:17][CH2:16]2)=[N:27][CH:28]=[C:29]([CH3:33])[CH:30]=1
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Komponenten

5

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 67272672(4-{[(3,5-Dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-3-hydroxymethyl-benzylamino)-acetic acid methyl ester

Produkt 2

HCID 14923Ammonium HydroxideHCID 672724662-(4-{[(3,5-Dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-3-hydroxymethyl-benzylamino)-ethanolAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (4-{[(3,5-Dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-3-hydroxymethyl-benzylamino)-acetic acid methyl ester (0.128 g, 0.26 mmol) in THF was added LiAlH4 (0.049 g, 1.30 mmol). The resulting slurry rapidly bubbled for the first minute and then gas production subsided. The mixture was stirred at room temperature for one hour and then was quenched with saturated aqueous NH4Cl (20 mL) and extracted with 98:2 (CHCl3/MeOH) (5×40 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to a pale yellow oil. Purification by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 85:10:5, v/v/v) afforded 2-(4-{[(3,5-dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-3-hydroxymethyl-benzylamino)-ethanol (0.045 g, 37%) as a colorless oil. 1H NMR (CDCl3) δ 1.58 (m, 1H), 1.98 (m, 2H), 2.16 (m, 1H), 2.21 (s, 3H), 2.25 (s, 3H), 2.64 (m, 1H), 2.78 (m+t, 3H), 3.61 (t, 2H, J=4.5 Hz), 3.65-3.72 (m, 3H), 3.75 (s, 2H), 3.88 (t, 1H, J=9.0 Hz), 4.15 (d, 2H, J=12.0 Hz), 4.36 (d, 1H, J=9.0 Hz), 7.01 (dd, 1H, J=7.5, 3.0 Hz), 7.16 (d, 1H, J=6.0), 7.21-7.32 (m, 4H), 8.16 (s, 1H), 8.36 (d, 1H, J=3.0 Hz). 13C NMR (CDCl3) δ 9.2, 26.5, 28.7, 28.8, 29.6, 42.9, 44.1, 79.7, 84.4, 86.5, 115.5, 121.8, 123.5, 124.6, 124.9, 130.8, 137.4, 140.1, 145.5, 155.1. HPLC: 99%. ES-MS m/z 461 [M+H]+.

Aufarbeitung

  1. customThe resulting slurry rapidly bubbled for the first minute
  2. customwas quenched with saturated aqueous NH4Cl (20 mL)
  3. extractionextracted with 98:2 (CHCl3/MeOH) (5×40 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a pale yellow oil
  7. customPurification by column chromatography on silica gel (CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-bc7d0d2a1cfc48ecbf165d2367e05bf7
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07863293B2

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