Ethyl 6'-bromo-1'-(1,1-dimethylethylsulfinamido)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylate → Ethyl 1'-amino-6'-bromo-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylate
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:27][CH2:26][CH:25]([O:28][CH3:29])[CH2:24][CH2:23]3)[C:8]2([NH:16]S(C(C)(C)C)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[NH2:16][C:8]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:10]=2)[CH2:6][C:7]21[CH2:23][CH2:24][CH:25]([O:28][CH3:29])[CH2:26][CH2:27]2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of compound 6 (40 mg, 0.11 mmol) in DCM (3 mL) was added TiCl4 (0.22 mL, 0.22 mmol) and the mixture was stirred in microwave at 50° C. for 10 min. After the reaction, bis-trimehtlysilylcarbodiimide (62 mg, 0.33 mmol) was added and the mixture was stirred in microwave at 60° C. for 10 min. The reaction was quenched with ice water and extracted with CH2Cl2, the organic layer was washed with water, brine, dried and concentrated to give the product 7 (20 mg, 57%).
Workup
- customAfter the reaction, bis-trimehtlysilylcarbodiimide (62 mg, 0.33 mmol)
- additionwas added
- stirringthe mixture was stirred in microwave at 60° C. for 10 min
- customThe reaction was quenched with ice water
- extractionextracted with CH2Cl2
- washthe organic layer was washed with water, brine
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e891050b40974eb5913b7e3a729f4621
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09212153B2
Reaction notes
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