Potassium Carbonate → HCID 18670412, compound

HRID 1059285Notes

Reaction equation

[CH3:1][O:2][CH2:3][Si](C)(C)C.C([Li])(CC)C.[CH3:13][C:14]12[C:22](=O)[C:18]([CH3:24])([CH2:19][CH2:20][CH2:21]1)[CH2:17][N:16]([CH3:25])[CH2:15]2.[Cl-].[NH4+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C1CCCCC1>[CH3:13][C:14]12[C:22](=[CH:3][O:2][CH3:1])[C:18]([CH3:24])([CH2:19][CH2:20][CH2:21]1)[CH2:17][N:16]([CH3:25])[CH2:15]2

Participants

Conditions

Temperature: -35 °C

Procedure

100 ml of a solution of 20.5 ml of (methoxymethyl)trimethylsilane in dry tetrahydrofuran was cooled under a nitrogen atmosphere. Then 92 ml of a 1.3 M solution of s-butyllithium in cyclohexane was added dropwise thereinto at −78° C. After the completion of the addition, the mixture was stirred at −35° C. for 30 minutes. After adding 10.9 g of 1,3,5-trimethyl-3-azabicyclo[3.3.1]nonan-9-one, the resulting mixture was stirred at room temperature for 2 hours and then poured into a cooled aqueous solution of ammonium chloride. Then it was made alkaline by adding potassium carbonate and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, 9.2 g of the title compound was obtained as a pale-brown oily substance.

Workup

customat −78° C
additionAfter the completion of the addition
stirringthe resulting mixture was stirred at room temperature for 2 hours
extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous sodium sulfate
distillationAfter distilling off the solvent under reduced pressure

Sources & evidence

ORD record: ord-0f436956cea34f95af81e319ef9e143f
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518423B1

Reaction notes

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