Tert-butyl 3-oxopiperidine-1-carboxylate → 1-Boc-3-ethynyl-3-hydroxypiperidine
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15]([Mg]Br)#[CH:16]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:15]#[CH:16])([OH:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 3-oxo-piperidine-1-carboxylic acid tert-butyl ester (112 mg, 0.56 mmol) in THF (1 mL) was added dropwise to a solution of ethynylmagnesium bromide (0.5 M, 2.2 mL) in THF (1 mL) at 0° C. and the resulting mixture was stirred at 0° C. for 4 hours. The reaction was quenched with saturated aqueous NH4Cl and extracted with ethyl acetate. The combined organic extracts were washed with water, brine, dried over anhydrous magnesium sulfate, and concentrated to afford 3-ethynyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (119 mg, 94%) as yellow oil. MS: m/z=226 amu (M++H).
Workup
- customThe reaction was quenched with saturated aqueous NH4Cl
- extractionextracted with ethyl acetate
- washThe combined organic extracts were washed with water, brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9148a75712e34f8cbe5dd486e99241d3
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07674791B2
Reaction notes
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