Methanol → HCID 68960167, compound

HRID 2376062Notes

Reaction equation

HRID 2376062 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([NH:20][C:21]2[CH:31]=[CH:30][C:24]([C:25](OCC)=[O:26])=[CH:23][N:22]=2)[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CO.O>O1CCCC1>[CH2:7]([N:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([NH:20][C:21]2[N:22]=[CH:23][C:24]([CH2:25][OH:26])=[CH:30][CH:31]=2)[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 68965049HCID 68965049, compound

Product 1

HCID 68960167HCID 68960167, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (70 mg, 1.8 mmol) in tetrahydrofuran (2 mL) was added a solution of ethyl 6-{[(3R)-1-benzyl-3-piperidinyl]amino}nicotinate (250 mg, 0.74 mmol) in tetrahydrofuran (5 mL) dropwise at 0° C. under nitrogen and the mixture was stirred at same temperature for 3 hrs. To the reaction mixture was added methanol and water dropwise at 0′ and the mixture was stirred for 1 h. The precipitate was removed by vacuum filtration and the filtrate was evaporated in vacuo. The residue was partitioned between water and ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated in vacuo to give (6-{[(3R)-1-benzyl-3-piperidinyl]amino}-3-pyridinyl)methanol (219 mg, 100%) as an oil.

Workup

  1. stirringwas stirred for 1 h
  2. customThe precipitate was removed by vacuum filtration
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was partitioned between water and ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-5a917993dae943f28af79d1d480593c1
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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