Triethylamine → 6-Methanesulfonyloxy-spiro[4.5]decane-7-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][CH2:13][CH2:12][C:7]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]1[OH:15])=[O:4].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:14][CH2:13][CH2:12][C:7]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]1[O:15][S:24]([CH3:23])(=[O:26])=[O:25])=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 6-hydroxy-spiro[4.5]decane-7-carboxylic acid methyl ester (10.1 g) obtained in Step 3 and triethylamine (19.9 mL) in chloroform (100 mL) was added dropwise methanesulfonyl chloride (5.2 mL) under ice-cooling, followed by stirring the reaction mixture at room temperature for 2 hours. Then, after addition of triethylamine (10 mL), the reaction mixture was stirred at room temperature for 30 minutes. After ice-cooling, ice-cold water (30 mL) and saturated aqueous sodium bicarbonate solution (50 mL) were added to the reaction mixture, followed by separation of the organic layer. The organic layer was washed with saturated brine, dried and concentrated to give a crude 6-methanesulfonyloxy-spiro[4.5]decane-7-carboxylic acid methyl ester (22 g).
Workup
- temperaturecooling
- stirringthe reaction mixture was stirred at room temperature for 30 minutes
- temperatureAfter ice-cooling
- customfollowed by separation of the organic layer
- washThe organic layer was washed with saturated brine
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-de9ee4fd15044adaa9116f8386be08c0
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299296B2
Reaction notes
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