Water → (2-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)pyridin-3-yl)methanol

HRID 1770795Notes

Reaction equation

HRID 1770795 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([O-])=[O:12])[CH2:2]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH:5]12[O:8][CH:1]([CH2:7][CH2:6]1)[CH2:2][N:3]([C:9]1[C:10]([CH2:11][OH:12])=[CH:14][CH:15]=[CH:16][N:17]=1)[CH2:4]2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 1317346412-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)nicotinate

Product 1

HCID 66369774(2-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)pyridin-3-yl)methanolYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)nicotinate (0.10 g, 0.40 mmol) in THF (5 mL) was added a solution of lithium aluminum hydride (1.2 mL, 1M in THF). The reaction mixture was stirred for 1 h and then 20 μL of H2O was added followed by 20 μL of 15% NaOH (aq) and then 60 μL of additional H2O. The slurry was stirred for 1 h, filtered and the resulting residue was washed with ether. The combined organic layers were dried over MgSO4 and concentrated in vacuo to yield (2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyridin-3-yl)methanol (0.070 g, 79% yield). MS (ES) for C12H16N2O2: 221 (MH+).

Workup

  1. stirringThe slurry was stirred for 1 h
  2. filtrationfiltered
  3. washthe resulting residue was washed with ether
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ce0afccae654e2995ba77e52062c8fd
Source dataset
uspto-grants-2016_02
Patent number
US09248199B2

Reaction notes

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