Potassium bis(trimethylsilyl)amide → HCID 57969620, compound

HRID 1920851Notes

Reaction equation

HRID 1920851 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[K+].[Br:11][C:12]1[CH:13]=[C:14]([C:18]2([CH:33]=O)[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:19]2)[CH:15]=[CH:16][CH:17]=1>C1COCC1>[Br:11][C:12]1[CH:13]=[C:14]([C:18]2([CH:33]=[CH2:1])[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:19]2)[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 57969637HCID 57969637, compound

Product 1

HCID 57969620HCID 57969620, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

KHMDS (0.5M in toluene, 6.536 mL, 3.268 mmol) was added to a suspension of Ph3PCH3Br (1.216 g, 3.404 mmol) in THF (15 mL) at rt. After 1 h, benzyl 3-(3-bromophenyl)-3-formylpyrrolidine-1-carboxylate was added at −20 and then the cold bath was removed. After 2 h, the reaction was quenched with MeOH (2 mL) and sat. aq. sodium bicarbonate was added. The mixture was extracted twice with ethyl acetate and then dried (MgSO4), filtered and concentrated.

Workup

  1. customthe cold bath was removed
  2. waitAfter 2 h
  3. customthe reaction was quenched with MeOH (2 mL) and sat. aq. sodium bicarbonate
  4. additionwas added
  5. extractionThe mixture was extracted twice with ethyl acetate
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0ab323f32d264648a05ad5179604ce8b
Source dataset
uspto-grants-2012_05
Patent number
US08173635B2

Reaction notes

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