Sodium Hydroxide → 1-[3-(Hydroxymethyl)-1-piperidinyl]-3-methyl-1-butanone
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1.[OH-].[Na+].[CH3:11][CH:12]([CH3:17])[CH2:13][C:14](Cl)=[O:15]>O.C1COCC1.CCOCC>[OH:8][CH2:7][CH:3]1[CH2:4][CH2:5][CH2:6][N:1]([C:14](=[O:15])[CH2:13][CH:12]([CH3:17])[CH3:11])[CH2:2]1Participants
Procedure
To a solution of piperidin-3-ylmethanol (10 g, 86.83 mmol) in water (25 mL), was added a solution of NaOH (13.89 g, 347.31 mmol) in water (25 mL) dropwise at 0° C. The mixture was stirred for 15 minutes, after which time, a solution of 3-methylbutanoyl chloride (20.94 g, 173.66 mmol) in THF (25 mL) was added dropwise with vigorous stirring. The reaction was slowly warmed to room temperature and, upon completion was diluted with Et2O (500 mL) was added with vigorous stirring. After 15 minutes, the phases were separated, and the aqueous phase was extracted with Et2O (2×). The combined organic extracts were washed with brine, dried over Na2SO4, concentrated under reduced pressure and flash chromatographed on silica gel (0-100% EtOAc in hexanes) to give the title compound as a colorless oil (16.27 g, 94%). MS 200 (MH+).
Workup
- additionwas added with vigorous stirring
- waitAfter 15 minutes
- customthe phases were separated
- extractionthe aqueous phase was extracted with Et2O (2×)
- washThe combined organic extracts were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure and flash
- customchromatographed on silica gel (0-100% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-7448e0b2c4934153bdfb4b4bd9232a83
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877922B2
Reaction notes
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