1-Iodopropane → HCID 46318390, compound
Reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[K+].[C:11]([N:18]1[CH2:23][CH2:22][CH:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].I[CH2:30][CH2:31][CH3:32]>C1COCC1>[CH2:27]([O:26][C:24]([C:21]1([CH2:30][CH2:31][CH3:32])[CH2:22][CH2:23][N:18]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:19][CH2:20]1)=[O:25])[CH3:28]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of potassium hexamethyldisilazide (29.1 g, 146 mmol) in THF (200 mL) at −78° C. was added ethyl N-Boc-piperidine-4-carboxylate (25 g, 97 mmol). The reaction mixture was stirred at −78° C. for 30 minutes, then 1-iodopropane (14.2 mL, 146 mmol) was slowly added. The reaction mixture was stirred at −78° C. for a further 20 minutes, then warmed to room temperature and stirred for 1 hour. The reaction was quenched by addition of saturated aqueous NH4Cl solution and extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (0% to 50% EtOAc in hexanes) to afford 19.3 g (66%) of 4-propyl-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester as a yellow oil.
Workup
- stirringThe reaction mixture was stirred at −78° C. for a further 20 minutes
- temperaturewarmed to room temperature
- stirringstirred for 1 hour
- customThe reaction was quenched by addition of saturated aqueous NH4Cl solution
- extractionextracted with EtOAc
- washThe combined organic extracts were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated under reduced pressure
- customThe residue was purified by flash chromatography (0% to 50% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-3e13ba24bc7345b9acf1be8d62be8b3d
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513425B2
Reaction notes
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