Sodium Bicarbonate → HCID 59226064, compound

HRID 2370274Notes

Reaction equation

HRID 2370274 reaction equation
[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][CH:7]1[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]([S:20]([NH2:22])=[O:21])([CH3:19])[CH3:18].C([O-])(O)=O.[Na+]>C1COCC1>[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][CH:7]1[CH2:12][CH2:11][C:10](=[N:22][S:20]([C:17]([CH3:19])([CH3:18])[CH3:16])=[O:21])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 3382465Tert-ButanesulfinamideHCID 106094304-(tert-Butyldimethylsilyloxy)cyclohexanone

Product 1

HCID 59226064HCID 59226064, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.00 g (21.9 mmol) of 4-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone in 100 mL THF was added 9.18 mL (43.8 mmol) of Ti(OEt)4 and 2.78 g (23.0 mmol) of 2-methyl-2-propanesulfinamide. The resulting mixture was stirred under reflux for 12 h, before being poured into an equal volume of saturated aqueous NaHCO3 with rapid stirring and filtered through celite. The filter cake was washed with ethyl acetate, the aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated under vacuum. The crude product was purified by silica gel chromatography to yield 5.12 g of the title compound (25) as diastereomeric mixture. Rt=1.87 min, 1.92 min (Method C). Detected mass: 332.3 (M+H+).

Workup

  1. temperatureunder reflux for 12 h
  2. stirringwith rapid stirring
  3. filtrationfiltered through celite
  4. washThe filter cake was washed with ethyl acetate
  5. customthe aqueous layer was separated
  6. extractionextracted twice with ethyl acetate
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c12676b3e0654bb4951a01b5b4b68e96
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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