tert-Butylsulfinamide, (S)-(-)- → HCID 178455880, compound

HRID 1433322Notes

Reaction equation

HRID 1433322 reaction equation
[CH3:1][C@H:2]([CH2:8][CH3:9])[CH2:3][CH2:4][C:5](=O)[CH3:6].[CH3:10][C:11]([S@@:14]([NH2:16])=[O:15])([CH3:13])[CH3:12]>O1CCCC1.C(OCC)(=O)C.[Cl-].[Na+].O.[O-]CC.[O-]CC.[O-]CC.[O-]CC.[Ti+4]>[CH3:6]/[C:5](=[N:16]\[S@:14]([C:11]([CH3:13])([CH3:12])[CH3:10])=[O:15])/[CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:8][CH3:9]

Participants

7

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 57935243HCID 57935243, compound

Product 1

HCID 178455880HCID 178455880, compound

Reagents, catalysts & solvents 4

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (5R)-5-methylheptan-2-one (3 g, 23.4 mmol) in tetrahydrofuran (10 ml) was added to a solution of (S)-2-methylpropane-2-sulfinamide and titanium tetraethoxide (9.8 ml, 46.8 mmol) in tetrahydrofuran. The solution was stirred at 50° C. for 20 hours. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate (50 ml) and then poured into brine (100 ml).

Workup

  1. temperatureto cool to room temperature

Sources & evidence

ORD record
ord-d9068e3594ac4283913d8ad2665c4a7e
Source dataset
uspto-grants-2009_11
Patent number
US07612226B2

Reaction notes

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