t-Butylaminodimethylsilylchloride → HCID 12149469, compound

HRID 1058219Notes

Reaction equation

HRID 1058219 reaction equation
[Li].[CH2:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([N:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)=[CH:3]1.[CH3:20][C:21]([NH:24][Si:25](Cl)([CH3:27])[CH3:26])([CH3:23])[CH3:22]>C1COCC1>[CH2:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][N:11]1[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:2]([Si:25]([CH3:27])([CH3:26])[NH:24][C:21]([CH3:23])([CH3:22])[CH3:20])[CH:3]=1

Participants

4

Reactant 2

HCID 11205972t-ButylaminodimethylsilylchlorideHCID 66768046HCID 66768046, compound

Product 1

HCID 12149469HCID 12149469, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,3-Dihydro-2-(1H-inden-3-yl)-1H-isoindole lithium salt (1.64 g, 6.86 mmol) was dissolved in 10 mL of THF and this solution was added dropwise to N-(tert-butyl)-N-(1-chloro-1,1-dimethylsilyl)amine reagent (1.47 g, 8.91 mmol, 1.3 eq) in 40 mL of THF. The reaction was allowed to stir for several hours, and THF and excess electrophile were removed under reduced pressure. The crude oil was extracted into hexane and filtered through a medium porosity frit. Solvent was removed under reduced pressure to give the desired product as an emerald green oil (2.40 g, 6.79 mmol, 96.5 percent).

Workup

  1. customTHF and excess electrophile were removed under reduced pressure
  2. extractionThe crude oil was extracted into hexane
  3. filtrationfiltered through a medium porosity frit
  4. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fa9cee30f6984ee4a8e119e56c197ca0
Source dataset
uspto-grants-2003_02
Patent number
US06515155B1

Reaction notes

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