Ammonium Chloride → HCID 66953702, compound

HRID 2096962Notes

Reaction equation

HRID 2096962 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

Methyllithium (1.6 M 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 10a, 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 (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. 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. customPurification of the residue by flash chromatography (97:3 dichloromethane/methanol)

Sources & evidence

ORD record
ord-7d9c2d44f2094cf28dec6727f4e72def
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

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