HCID 12030321, compound → HCID 66790620, compound

HRID 1510145Notes

Reaction equation

HRID 1510145 reaction equation
[CH3:1][Si:2]1([CH3:18])[CH2:7][CH:6]2[CH:4]([N:5]2[S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][Si:2]1([CH3:18])[CH2:7][CH2:6][CH:4]([NH:5][S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:3]1

Participants

4

Reactant 2

HCID 12030321HCID 12030321, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 66790620HCID 66790620, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 3,3-dimethyl-6-[(4-methylphenyl)sulfonyl]-6-aza-3-silabicyclo[3.1.0]hexane (0.5 g, 1.8 mmol) in THF (10 ml) was added lithium aluminum hydride (11.0M THF, 5.33 mL, 5.33 mol). After stirring at rt overnight, the reaction was quenched by the sequential addition of H2O (0.2 mL), 1N NaOH (0.2 mL), and H2O (0.6 mL). The mixture was filtered through a pad of celite and concentrated under vacuum. Purification by silica gel chromatography (20% EtOAc/hexanes) afforded the desired product.

Workup

  1. customthe reaction was quenched by the sequential addition of H2O (0.2 mL), 1N NaOH (0.2 mL), and H2O (0.6 mL)
  2. filtrationThe mixture was filtered through a pad of celite
  3. concentrationconcentrated under vacuum
  4. customPurification by silica gel chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-31e61e178552426685c9d18c38e7cb11
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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