Methanol → 6'-Chloro-1',2'-dihydrospiro(cyclopropane-1,3'-indole)
Reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH2:13][CH2:12]3)[C:7](=O)[NH:8]2)=[CH:4][CH:3]=1.CO>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH2:13][CH2:12]3)[CH2:7][NH:8]2)=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 6′ chloro-spiro[cyclopropane-1,3′-[3H]indol]-2′(1′H)-one (0.291 g, 1.5 mmol) and borane-dimethyl sulfide complex in THF (2 M, 3.0 mL) was heated at reflux under nitrogen for 2 h. The mixture was cooled and MeOH (3 mL) was added dropwise (caution!). The resulting mixture was heated at reflux for 2 h, then was cooled and solvent evaporated in vacuo. Chromatography (SiO2; gradient elution with 0-100% Et2O in petrol) gave the title compound (0.142 g). MS: [M+H]+=180.
Workup
- temperaturewas heated
- temperatureat reflux under nitrogen for 2 h
- temperatureThe mixture was cooled
- temperatureThe resulting mixture was heated
- temperatureat reflux for 2 h
- temperaturewas cooled
- customsolvent evaporated in vacuo
- washChromatography (SiO2; gradient elution with 0-100% Et2O in petrol)
Sources & evidence
- ORD record
- ord-591e33db7ac24a28b307ca4401e38525
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018214B2
Reaction notes
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