Sodium Methoxide → HCID 68543391, compound

HRID 1441675Notes

Reaction equation

HRID 1441675 reaction equation
CC([O:4][CH2:5][CH2:6][N:7]1[C:20]2[C:15](=[CH:16][C:17]([CH2:21][CH:22]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:18][CH:19]=2)[C:9]2([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[C:8]1=[O:30])=O.C[O-].[Na+]>CO>[OH:4][CH2:5][CH2:6][N:7]1[C:20]2[C:15](=[CH:16][C:17]([CH2:21][CH:22]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:18][CH:19]=2)[C:9]2([CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[C:8]1=[O:30]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 68542733HCID 68542733, compound

Product 1

HCID 68543391HCID 68543391, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1-(methylcarbonyloxy-ethyl)-5(cyclooctyl-methyl)-spiro[indoline-3,4′-piperidin]-2-one (0.012 g, 0.028 mmol) was dissolved in methanol (1.5 mL). To the reaction mixture was then added at room temperature a 25% solution of sodium methoxide in methanol (50 μL) and the reaction mixture was stirred for 30 minutes. The solvent was evaporated in vacuo to yield an oil which was then partitioned with aqueous 0.1N HCl and dichloromethane. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (35% ethyl acetate/hexanes) to yield the title compound as an oil.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto yield an oil which
  3. customwas then partitioned with aqueous 0.1N HCl and dichloromethane
  4. washThe organic layer was washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customto yield a crude oil
  9. customThe crude oil was purified via flash chromatography (35% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-113080f36ada454592087108a5bf6792
Source dataset
uspto-grants-2010_02
Patent number
US07655670B2

Reaction notes

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