Ammonium Chloride → Ethyl 4'-fluorospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-carboxylate
Reaction equation
[C:1]12([O:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[O:12]1)[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]2.C([N-]C(C)C)(C)C.[Li+].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:38])(=O)=O)=CC=1.[NH4+].[Cl-]>O1CCCC1>[F:38][C:4]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2][C:1]2([O:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[O:15]2)[CH2:6][CH2:5]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of EXAMPLE 350A (5.25 g) in tetrahydrofuran (40 mL) was added dropwise to a solution of lithium diisopropylamide (12 mL, 2.0M in tetrahydrofuran/heptane/ethylbenzene) at 0° C. The solution was stirred at 0° C. for 30 minutes, and then was transferred by cannula to a pre-cooled (0° C.) stirring solution of N-fluorobenzenesulfonimide (7.89 g) in dry tetrahydrofuran (20 mL). The reaction mixture was stirred at 0° C. for 30 minutes, and then at 20° C. for 18 hours. The reaction mixture was poured over aqueous NH4Cl and extracted with diethyl ether (3×200 mL). The combined organic layers were washed with water, brine and dried over Na2SO4. Filtration and evaporation of the solvent gave the crude product.
Workup
- temperaturea pre-cooled (0° C.)
- stirringThe reaction mixture was stirred at 0° C. for 30 minutes
- waitat 20° C. for 18 hours
- extractionextracted with diethyl ether (3×200 mL)
- washThe combined organic layers were washed with water, brine
- dry with materialdried over Na2SO4
- filtrationFiltration and evaporation of the solvent
Sources & evidence
- ORD record
- ord-effdd4bc8d354e9ca39e14bb8169ccac
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045475B2
Reaction notes
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