956141-90-5 → 5-Chloro-2,3-dihydrospiro[1H-indene-1,3′-pyrrolidine]
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[C:7]1([CH2:11][C:10](=O)[NH:9][C:8]1=O)[CH2:6][CH2:5]2>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[C:7]1([CH2:11][CH2:10][NH:9][CH2:8]1)[CH2:6][CH2:5]2Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 5-chloro-2,3-dihydrospiro[indene-1,3′-pyrrolidine]-2′,5′-dione (Prep7, 3 g, 12.7 mmol) in anhydrous THF (20 ml) at 0° C. and under a nitrogen atmosphere, BH3(CH3)2S complex in THF (1M, 50 ml) was added dropwise. The ice-bath was removed, the reaction mixture was allowed to reach room temperature and refluxed for 28 h. The mixture was then cooled to 0° C. and hydrochloric acid (2 M, 30 ml) was cautiously added monitoring gas evolution, then the ice-bath was removed and the reaction was stirred for 1 h. THF was then removed in vacuo, the residue was cooled to 0° C. DCM was added and the stirred mixture was treated with a solution of NaOH (2M) until pH=13. The mixture was extracted with additional DCM, the solvent was evaporated under vacuum to obtain the crude title compound (3 g).
Workup
- customThe ice-bath was removed
- customto reach room temperature
- temperaturerefluxed for 28 h
- customthe ice-bath was removed
- customTHF was then removed in vacuo
- temperaturethe residue was cooled to 0° C
- additionDCM was added
- additionthe stirred mixture was treated with a solution of NaOH (2M) until pH=13
- extractionThe mixture was extracted with additional DCM
- customthe solvent was evaporated under vacuum
Sources & evidence
- ORD record
- ord-01681833270141029494f4e19071e077
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030322B2
Reaction notes
Loading…