HCID 86651805, compound → HCID 69809727, compound

HRID 2190038Notes

Reaction equation

HRID 2190038 reaction equation
CON(C)[C:4]([C@H:6]1[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][C@@:8]2([C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][C:18]2=[O:26])[CH2:7]1)=[O:5].[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([Mg]Br)=[CH:31][CH:30]=1>C1COCC1>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:4]([C@H:6]2[N:10]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH2:9][C@@:8]3([C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][C:18]3=[O:26])[CH2:7]2)=[O:5])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 86651805HCID 86651805, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 69809727HCID 69809727, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (3S,5′S)-tert-butyl 5′-(methoxy(methyl)carbamoyl)-2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (310 mg, 0.826 mmol) in THF (4 mL) was added 4-chloro phenylmagnesium bromide (1.0 N in THF, 2.89 mL, 2.89 mmol) at about 0° C. The reaction mixture was warmed to about room temperature and stirred overnight. The reaction was quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The crude product was purified by column chromatography (hexanes:EtOAc, 1:1) to give (3S,5′S)-tert-butyl 5′-(4-chlorobenzoyl)-2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (0.240 g, 68%). LCMS (APCI+) m/z 427, 429 [M+H]+; Rt=3.94 min.

Workup

  1. temperatureThe reaction mixture was warmed to about room temperature
  2. customThe reaction was quenched with saturated aqueous NH4Cl solution
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (hexanes:EtOAc, 1:1)

Sources & evidence

ORD record
ord-5894bbba8e2c4153b480e5009cafc47e
Source dataset
uspto-grants-2012_12
Patent number
US08324221B2

Reaction notes

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