Acetaldehyde → HCID 21912733, compound
Reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[CH:32](=[O:34])[CH3:33]>C1COCC1>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([CH:26]([CH:32]([OH:34])[CH3:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of 0.35 mL (2.5 mmol) of diisopropylamine in 10 mL of THF at 0° C. was treated with 1.6 mL of 1.0 M n-butyllithium solution in hexanes. The resulting mixture was stirred at 0° C. for 10 min, then cooled to −78° C. A solution of 540 mg (2.0 mmol) of ethyl 2-(1-tert-butoxycarbonyl-piperidin-4-yl)acetate (from Piperidine 35, Step A) in 2 mL of THF was added and the resulting solution was stirred cold for 30 min. Acetaldehyde (0.17 mL, 3.0 mmol) was added and the resulting mixture was warmed to 0° C. The reaction was quenched with 10 mL of sat'd NH4Cl and the resulting mixture was partitioned between 50 mL of ether and 25 mL of water. The organic layer was separated, dried over MgSO4 and concentrated. Flash chromatography on 20 g of silica gel using 2:1 v/v hexanes/EtOAc as the eluant afforded the title compound.
Workup
- temperaturecooled to −78° C
- stirringthe resulting solution was stirred cold for 30 min
- temperaturethe resulting mixture was warmed to 0° C
- customThe reaction was quenched with 10 mL of sat'd NH4Cl
- customthe resulting mixture was partitioned between 50 mL of ether and 25 mL of water
- customThe organic layer was separated
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1a31d65c94444ed7989e5e310f346948
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07125887B2
Reaction notes
Loading…