Potassium trimethylsilanolate → Potassium [(2S)-2-(3,5-difluorophenyl)-2,5,5-trimethyl-6-oxopiperidin-1-yl]acetate

HRID 1367246Notes

Reaction equation

HRID 1367246 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@:9]2([CH3:23])[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[C:11](=[O:17])[N:10]2[CH2:18][C:19]([O:21]C)=[O:20])[CH:5]=[C:6]([F:8])[CH:7]=1.C[Si](C)(C)[O-].[K+:29]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C@:9]2([CH3:23])[CH2:14][CH2:13][C:12]([CH3:15])([CH3:16])[C:11](=[O:17])[N:10]2[CH2:18][C:19]([O-:21])=[O:20])[CH:5]=[C:6]([F:8])[CH:7]=1.[K+:29]

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolate2×HCID 57974130Methyl [(2S)-2-(3,5-difluorophenyl)-2,5,5-trimethyl-6-oxopiperidin-1-yl]acetate

Product 1

HCID 66973013Potassium [(2S)-2-(3,5-difluorophenyl)-2,5,5-trimethyl-6-oxopiperidin-1-yl]acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl [(2S)-2-(3,5-difluorophenyl)-2,5,5-trimethyl-6-oxopiperidin-1-yl]acetate from Step D (298 mg, 0.916 mmol) in THF (9 mL) at ambient temperature was added potassium trimethylsilanolate (147 mg, 1.14 mmol). The reaction was stirred for 24 hours and found to be incomplete by LCMS analysis. Additional quantities of potassium trimethylsilanolate were added as needed. The reaction was concentrated in vacuo to give a residue that required no further purification. MS: m/z=312 (M+1 for parent acid).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customto give a residue that
  3. customno further purification

Sources & evidence

ORD record
ord-f76b992b829e427b9ed26a58772f489b
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

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