methyl 5-morpholinonicotinate → [5-(Morpholin-4-yl)pyridin-3-yl]methanol

HRID 1174512Notes

Reaction equation

HRID 1174512 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([CH:22]=2)[C:18](OC)=[O:19])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1>C1COCC1>[N:7]1([C:13]2[CH:22]=[C:17]([CH2:18][OH:19])[CH:16]=[N:15][CH:14]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 355238methyl 5-morpholinonicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 59557819[5-(Morpholin-4-yl)pyridin-3-yl]methanolYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LAH (1 g, 0.027 mol) in dry THF (70 mL) was added methyl 5-morpholin-4-ylnicotinate (4 g, 0.018 mol) in dry THF (10 mL) at −40° C. under stirring. The reaction mixture was stirred at this temperature for 2 h and then quenched with 6 mL of 10% aqueous NaOH solution at −40° C. The reaction mixture was allowed to stir at RT for 30 min, filtered through celite, washed with THF and concentrated to afford 2.8 g, (80%) of the title compound as a liquid.

Workup

  1. stirringThe reaction mixture was stirred at this temperature for 2 h
  2. customquenched with 6 mL of 10% aqueous NaOH solution at −40° C
  3. stirringto stir at RT for 30 min
  4. filtrationfiltered through celite
  5. washwashed with THF
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e49c3c2c48a24550bf003f6723275a35
Source dataset
uspto-grants-2010_11
Patent number
US07838522B2

Reaction notes

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