Dichloromethane → (1S,2R)-2-(2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)acetaldehyde
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C@:10]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH2:19][CH:20](OC)[O:21]C)[C:11]3=[O:25])[CH2:9]2)=[CH:4][CH:3]=1.C(Cl)Cl.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[C@:10]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH2:19][CH:20]=[O:21])[C:11]3=[O:25])[CH2:9]2)=[CH:6][CH:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A suspension of (1R,2S) and (1S,2R)-2-(4-chlorophenyl)-1′-(2,2-dimethoxyethyl) spiro[cyclopropane-1,3′-indolin]-2′-one (1 g) in water (1 mL) was cooled to 0° C. and treated with a mixture of DCM and TFA (1:1, 6 mL) for 2 hours. The reaction mixture was poured into saturated aq. NaHCO3 solution and extracted with DCM (3×6 mL). The combined organic layers were washed with brine and dried over Na2SO4. The solvent was evaporated under reduced pressure. The crude product was used for next step directly without any further purification. LC/MS m/e calcd. for C18H14ClNO2: 311, observed (M+H)+: 312.3.
Workup
- extractionextracted with DCM (3×6 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- customThe solvent was evaporated under reduced pressure
- customThe crude product was used for next step directly without any further purification
Sources & evidence
- ORD record
- ord-973ce012ac004f74aebe3b2c1df5a710
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354443B2
Reaction notes
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