Hydrochloric Acid → Allyl-((R)-1-methyl-pent-4-enyl)-carbamic acid benzyl ester
Reaction equation
[CH2:1]([O:8][C:9](=[O:17])[NH:10][C@H:11]([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:20](Br)[CH:21]=[CH2:22].Cl>CN(C=O)C.O>[CH2:1]([O:8][C:9](=[O:17])[N:10]([CH2:22][CH:21]=[CH2:20])[C@H:11]([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
((R)-1-Methyl-pent-4-enyl)-carbamic acid benzyl ester (790 mg, 3.39 mmol) was dissolved in DMF (8 ml) and was cooled to 0 degrees C. Sodium hydride (60% dispersion, 271 mg, 6.78 mmol) was added and the reaction was stirred for 15 minutes. Allyl bromide (1.23 g, 0.88 ml, 10.17 mmol) was added and the reaction mixture was stirred for 3 h at 0 degrees C. H2O (10 ml) was added, then 2N HCl was added dropwise adjusting the pH to 1. The reaction mixture was extracted with Et2O (2×50 ml). The combined organics were washed with aq. 2N HCl, then aq. NaHCO3, then brine. The combined organics were dried with MgSO4, filtered, concentrated in vacuo, then chromatographed on silica gel (5% EtOAc/hexanes) to yield the title compound as a colorless oil (883 mg, 95%).
Workup
- stirringthe reaction mixture was stirred for 3 h at 0 degrees C
- extractionThe reaction mixture was extracted with Et2O (2×50 ml)
- washThe combined organics were washed with aq. 2N HCl
- dry with materialThe combined organics were dried with MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customchromatographed on silica gel (5% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-4294699cb9bb4ec5aea0bdb139009f57
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07563784B2
Reaction notes
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