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Dichloromethane → (1S,2R)-2-(2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)acetaldehyde

HRID 1805326
Notes
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Reaction equation

HRID 1805326 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 58305319(1S,2R)-2-(4-chlorophenyl)-1'-(2,2-dimethoxyethyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58305328(1S,2R)-2-(2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. extractionextracted with DCM (3×6 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated under reduced pressure
  5. 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08354443B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes