Aluminium lithium hydride → (2S)-1,2,3,6-Tetrahydro-4-(4-methoxyphenyl)-2-pyridinemethanol

HRID 2246935Notes

Reaction equation

HRID 2246935 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:14][C:15]([C@@H:17]1[CH2:22][C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[CH:20][C:19](=O)[NH:18]1)=O)C1C=CC=CC=1>O1CCCC1>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([C:21]2[CH2:22][C@@H:17]([CH2:15][OH:14])[NH:18][CH2:19][CH:20]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68441392HCID 68441392, compound

Product 1

HCID 68443118(2S)-1,2,3,6-Tetrahydro-4-(4-methoxyphenyl)-2-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 10.9 g of lithium aluminium hydride in 1 l of tetrahydrofuran is added a solution of 43 g of (S)-4-(4-methoxy-phenyl)-6-oxo-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid benzyl ester in 1 l of tetrahydrofuran at 70° C. The reaction mixture is stirred for another 3-4 hours at this temperature, cooled to 0° C. and quenched by the slow addition of 12.4 ml of water, 12.4 ml of 2N sodium hydroxide and 37 ml of water. The mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a white solid. Rf=0.17 (dichloromethane-methanol-25% ammonia conc. 90:10:1); Rt=2.55.

Workup

  1. customquenched by the slow addition of 12.4 ml of water, 12.4 ml of 2N sodium hydroxide and 37 ml of water
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-e2518f6a14514eef95cc558f261d2a36
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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