Diisopropylamine → HCID 54328520, compound
Reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])C.C1C[O:11]CC1.[CH2:13]([Li])[CH2:14][CH2:15][CH3:16].C(O[C:21](=[O:36])[CH:22]([CH2:29][C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1)[CH2:23][C:24]1[CH:28]=[CH:27][O:26][CH:25]=1)C.[CH3:37][CH2:38][CH2:39]CCC>>[C:5]12([N:4]3[C:1](=[O:11])[CH2:3][C:22]([CH2:23][C:24]4[CH:28]=[CH:27][O:26][CH:25]=4)([CH2:29][C:30]4[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=4)[C:21]3=[O:36])[CH2:6][CH:13]3[CH2:37][CH:38]([CH2:39][CH:15]([CH2:14]3)[CH2:16]1)[CH2:7]2Participants
6
Conditions
- Temperature
- -78 °C
Procedure
Under a nitrogen atmosphere were combined diisopropylamine (2.72 ml, 6.79 mmol) and anhydrous THF (30 mls), and the solution was cooled to -78° C. 2.5M butyl lithium (2.72 ml, 6.79 mmol) was added and the solution was allowed to warm to about 3-furan-3-yl-2-pyridin4-ylmethyl propionic acid ethyl ester (2.20 g (80% pure), 6.79 mmol) was added dropwise and the solution was stirred at -78° C. for 1 hour. To this solution was added 1.85 g (6.79 mmol) of N-adamantyl-1-yl-2-bromo-acetamide at -78° C. and the mixture was kept at -78° C. for 16 hours and then warmed to room temperature for 3 hours. The standard reaction workup after silica gel chromatography (1:1 EtOAC:hexane) provided 300 mg of the title compound.
Workup
- additionwas added dropwise
- waitthe mixture was kept at -78° C. for 16 hours
- temperaturewarmed to room temperature for 3 hours
Sources & evidence
- ORD record
- ord-669aaff98470490b8bc954a6c88fc584
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05854232
Reaction notes
Loading…