Ammonium Chloride → HCID 90449861, compound

HRID 1411303Notes

Reaction equation

HRID 1411303 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:22]([O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])=[O:23])[C:5]2=[CH:6][CH:7]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[Br-].[CH2:61]([O:63][C:64](=[O:69])[CH2:65][CH2:66][CH2:67][Zn+])[CH3:62].[Cl-].[NH4+]>O1CCCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH2:61]([O:63][C:64](=[O:69])[CH2:65][CH2:66][CH2:67][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:22]([O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])=[O:23])[C:5]2=[CH:6][CH:7]=1)[CH3:62]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 90449581HCID 90449581, compoundHCID 178471550HCID 178471550, compound

Product 1

HCID 90449861HCID 90449861, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-bromospiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (100 mg, 0.201 mmol) obtained in Step 2 of Example 383 was dissolved in tetrahydrofuran (1.5 mL). Thereafter, palladium diacetate (10.0 mg, 0.045 mmol), S-Phos (33.0 mg, 0.080 mmol), and 4-ethoxy-4-oxobutylzinc bromide (0.5 M tetrahydrofuran solution, 0.5 mL) were added to the above obtained solution at room temperature, and the thus obtained mixture was then stirred at room temperature for 14 hours. Thereafter, a saturated aqueous solution of ammonium chloride was added to the reaction solution, and the mixed solution was then extracted with chloroform. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (hexane ethyl acetate=10:1) to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(4-ethoxy-4-oxobutyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (75.2 mg, 70%.) in the form of a white solid.

Workup

  1. extractionthe mixed solution was then extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. concentrationfollowed by concentration in vacuo
  5. customThe obtained residue was purified by silica gel column chromatography (hexane ethyl acetate=10:1)

Sources & evidence

ORD record
ord-07532465253d4cb1b5a5ff8072295bb6
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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