Sodium Carbonate → N-(8-benzyl-8-aza-bicyclo[3.2.1]octan-3-yl)isobutyramide
Reaction equation
[CH2:1]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([NH2:16])[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:23](Cl)(=[O:27])[CH:24]([CH3:26])[CH3:25]>C(Cl)Cl>[CH2:1]([N:8]1[CH:9]2[CH2:15][CH2:14][CH:13]1[CH2:12][CH:11]([NH:16][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[CH2:10]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a solution of amine 100 (2.70 g, 12.48 mmol) in CH2Cl2 (13 mL), was added 1M Na2CO3 (19 mL, 18.72 mmol, 1.5 equiv). The mixture was cooled to 0° C. and isobutyryl chloride (1.6 mL, 14.98 mmol, 1.2 equiv) was added dropwise with stirring over 30 min. The resulting mixture was warmed to room temperature and allowed to stir for 2 h after which time the layers were separated and the aqueous layer was extracted with CH2Cl2 (3×25 mL). The combined organic layers were washed with 1N NaOH (2×20 mL), then with H2O (2×20 mL), then dried over MgSO4, filtered, and concentrated in vacuo to yield amide 101 (3.3 g, 93%).
Workup
- temperatureThe resulting mixture was warmed to room temperature
- stirringto stir for 2 h after which time the layers
- customwere separated
- extractionthe aqueous layer was extracted with CH2Cl2 (3×25 mL)
- washThe combined organic layers were washed with 1N NaOH (2×20 mL)
- dry with materialwith H2O (2×20 mL), then dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-de0087e0cebb400ba66c5bb5a4c0e4a5
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932235B2
Reaction notes
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