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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
Notes
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Reaction equation

HRID 251277 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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

Product 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)-ethanolYield 75.2%

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-bc7d0d2a1cfc48ecbf165d2367e05bf7
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863293B2

Reaction notes

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