Ammonium Chloride → HCID 66953702, compound

HRID 1619113Notes

Reaction equation

HRID 1619113 reaction equation
[CH3:1][Li].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]3([CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]3)[C:9](=[O:13])[NH:10]2)=[CH:6][CH:5]=1.[Cl-].[NH4+]>O1CCCC1>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]3([CH2:14][CH2:15][C:16]([OH:19])([CH3:1])[CH2:17][CH2:18]3)[C:9](=[O:13])[NH:10]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 66953983HCID 66953983, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 66953702HCID 66953702, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl lithium (1.6M in diethyl ether, 4.89 mL, 7.82 mmol) was added dropwise to a stirred solution of 6′-bromospiro[cyclohexane-1,3′-indoline]-2′,4-dione (preparation 21a, 1.00 g, 3.40 mmol) in tetrahydrofuran (30 mL) at −78° C. The mixture was warmed to 0° C. over 3 hours and stirred at room temperature for additional 4.5 hours. Saturated aqueous ammonium chloride solution (20 mL) was added to the reaction and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated to give a mixture of isomers of the title compound. Purification of the residue by flash chromatography (97:3 dichloromethane/methanol) gave the two pure isomers of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give

Sources & evidence

ORD record
ord-4026910fab0e4b0ea711f422b55ccd7c
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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