Acetic Acid → Methyl 9-oxobicyclo[3.3.1]nonane-3-carboxylate
Reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH:4]([CH2:7]Br)[CH2:5]Br.[C:10]1(N2CCCC2)[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=1.C(N(CC)CC)C.C(O)(=[O:30])C>CC#N.O>[CH3:1][O:2][C:3]([CH:4]1[CH2:7][CH:11]2[C:10](=[O:30])[CH:15]([CH2:14][CH2:13][CH2:12]2)[CH2:5]1)=[O:9]Participants
Conditions
- Temperature
- 100 °C
Procedure
3-Bromo-2-bromomethyl-propionic acid methyl ester (30 g, 115 mmol) was added to a stirred solution of freshly distilled 1-cyclohex-1-enyl-pyrrolidine (20.4 mL, 126 mmol) and triethyl amine (35 mL, 252 mmol) in dry CH3CN (400 mL). After the addition, the mixture was heated (100° C.) and stirred for twelve hours before acetic acid (20 mL) and water (100 mL) were added. Then, heating was continued for another three hours. The solvent was evaporated and the residue was partitioned with diethyl ether and water. The organic phase was washed with a NaHCO3 solution until the washes became basic. It was then dried, filtered, and evaporated. The residue was purified over silica gel using 2-30% diethyl ether in hexanes to give the title compound as a clear oil.
Workup
- additionAfter the addition
- additionwere added
- temperatureThen, heating
- customThe solvent was evaporated
- customthe residue was partitioned with diethyl ether and water
- washThe organic phase was washed with a NaHCO3 solution until the washes
- customIt was then dried
- filtrationfiltered
- customevaporated
- customThe residue was purified over silica gel using 2-30% diethyl ether in hexanes
Sources & evidence
- ORD record
- ord-499dc9a566d3415a9db0ac30f2538769
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737137B2
Reaction notes
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