D-Proline → Chloro(1-quinolin-6-ylcyclopropyl)acetaldehyde
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3([CH2:14][CH:15]=[O:16])[CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.N1CCC[C@@H]1C(O)=O.[Cl:25]N1C(=O)CCC1=O>ClCCl>[Cl:25][CH:14]([C:11]1([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:1]=[CH:2][CH:3]=[CH:4]3)[CH2:12][CH2:13]1)[CH:15]=[O:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of (1-quinolin-6-ylcyclopropyl)acetaldehyde (410 mg, 1.94 mmol), D-proline (45 mg, 0.39 mmol) in dichloromethane (10 mL) cooled (0° C.) was added N-chlorosuccinimide (311 mg, 2.33 mmol) with stirring. The reaction mixture was stirred at 0° C. for 1 h, then gradually warmed to RT. The reaction mixture was quenched with water, extracted with dichloromethane. The combined organic extracts were concentrated and the residue purified by flash chromatography eluting with ethyl acetate in hexanes (0-25% in 18 min) to afford the desired product. (320 mg, 67.1%) LCMS: (M+H)=246.2; (M+H2O+H)=264.2.
Workup
- stirringThe reaction mixture was stirred at 0° C. for 1 h
- temperaturegradually warmed to RT
- customThe reaction mixture was quenched with water
- extractionextracted with dichloromethane
- concentrationThe combined organic extracts were concentrated
- customthe residue purified by flash chromatography
- washeluting with ethyl acetate in hexanes (0-25% in 18 min)
Sources & evidence
- ORD record
- ord-633c4f352ebe4a3996cfe242058e6945
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767675B2
Reaction notes
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