Methanol → Methyl 3-acetyladamantane-1-carboxylate
Reaction equation
[CH3:1][Li].[CH3:3][O:4][C:5]([C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][C:9]([C:17](Cl)=[O:18])([CH2:10]3)[CH2:8]1)[CH2:14]2)=[O:6].CO.[Cl-].[NH4+]>[Cu]I.CCOCC>[C:17]([C:9]12[CH2:15][CH:13]3[CH2:12][CH:11]([CH2:16][C:7]([C:5]([O:4][CH3:3])=[O:6])([CH2:14]3)[CH2:8]1)[CH2:10]2)(=[O:18])[CH3:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
Under nitrogen, a chilled (0° C.) diethyl ether suspension of copper (I) iodide (3.0 eq) was treated with methyl lithium (6.0 eq, 1.4 M in ethyl ether). The resulting solution was chilled to −78° C. and after ten minutes a chilled (−30° C.) diethyl ether solution of 3-methoxycarbonyladamantane-1-carboxylic acid chloride was added dropwise over a five minute period. The reaction was stirred for 45 minutes at −78° C. and then quenched with MeOH (11.0 eq) and allowed to warm to room temperature. After addition of Et2O and saturated aqueous ammonium chloride solution, the mixture was stirred for ten minutes and then the organic phase was washed with saturated NH4Cl, saturated NaHCO3, brine, dried (MgSO4), filtered and concentrated to a volatile oil, which was used without further purification.
Workup
- temperatureUnder nitrogen, a chilled
- additionwas added dropwise over a five minute period
- temperatureto warm to room temperature
- stirringthe mixture was stirred for ten minutes
- washthe organic phase was washed with saturated NH4Cl, saturated NaHCO3, brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated to a volatile oil, which
- customwas used without further purification
Sources & evidence
- ORD record
- ord-0448677bf9ee464f9269940256cc6377
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115768B2
Reaction notes
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