Methanol → HCID 68960167, compound
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]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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° C. 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
- stirringthe mixture was stirred for 1 h
- customThe precipitate was removed by vacuum filtration
- customthe filtrate was evaporated in vacuo
- customThe residue was partitioned between water and ethyl acetate
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-522e042167c74120a038979dedbf37de
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557127B2
Reaction notes
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