Allyl bromide → HCID 58573467, compound

HRID 931945Notes

Reaction equation

HRID 931945 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:9](=[O:28])[C@:10]3([C@@H:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][CH2:13][C:12](=[O:23])[N:11]3[CH2:24][CH:25]3[CH2:27][CH2:26]3)[C:5]2=[CH:4][CH:3]=1.[Li+].[CH3:38][CH:39]([N-]C(C)C)[CH3:40].C(Br)C=C>C1COCC1>[CH2:40]([C@@H:13]1[C:12](=[O:23])[N:11]([CH2:24][CH:25]2[CH2:26][CH2:27]2)[C@:10]2([C:5]3[C:6](=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:8]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:9]2=[O:28])[C@@H:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[CH2:14]1)[CH:39]=[CH2:38]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 2724682Lithium diisopropylamideHCID 58573102HCID 58573102, compound

Product 1

HCID 58573467HCID 58573467, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of (rac) (2′S,3′R)-6-chloro-3′-(3-chlorophenyl)-1′-(cyclopropylmethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)spiro[indoline-3,2′-piperidine]-2,6′-dione (Example 62, Step I) (97 mg, 0.178 mmol) in THF (1 mL) at −78° C. under Ar was added freshly prepared LDA (1.0 M in THF) (178 μL, 0.178 mmol). The reaction color turned yellowish orange. The reaction was stirred at −78° C. for 30 min then distilled allyl bromide (15.39 μL, 0.178 mmol) was added. The reaction was stirred at −78° C. for 10 min then warmed to 0° C. The reaction was quenched with sat. NH4Cl and warmed to room temperature. The mixture was diluted with EtOAc and the layers were separated. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent: 0 to 25% EtOAc in hexanes) to give the title compound.

Workup

  1. stirringThe reaction was stirred at −78° C. for 10 min
  2. temperaturethen warmed to 0° C
  3. customThe reaction was quenched with sat. NH4Cl
  4. temperaturewarmed to room temperature
  5. additionThe mixture was diluted with EtOAc
  6. customthe layers were separated
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography on silica gel (eluent: 0 to 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7e0c0ae5f79c40c4bb2a9e0beca01742
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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