Borane;tetrahydrofuran → HCID 59550891, compound

HRID 1169717Notes

Reaction equation

HRID 1169717 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:17])(=[N:12][C:13](=O)[CH2:14][CH3:15])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].B.O1CCCC1.O.CO>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH3:17])(=[N:12][CH2:13][CH2:14][CH3:15])=[O:11])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 2723981Borane;tetrahydrofuranHCID 22242641Methanol--water (1/1)HCID 59550888HCID 59550888, compound

Product 1

HCID 59550891HCID 59550891, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

351 mg (1.37 mmol) (RS)—S-(4-nitrophenyl)-N-propionyl-S-methylsulfoximide (Example 9a) are dissolved in 15 ml dichloromethane and treated dropwise with borane-tetrahydrofuran complex (1.0 M solution in tetrahydrofuran, Aldrich) with ice-cooling. The mixture is stirred for 3 hours at 0° C. Next it is cautiously treated with ca. 10 ml water/methanol (1:1), stirred for 30 minutes and extracted with dichloromethane. The organic phase is dried over sodium sulphate and concentrated. After chromatographic purification (silica gel, hexane/ethyl acetate (0-50% ethyl acetate)), 146 mg (44%) of the desired product is obtained.

Workup

  1. temperaturecooling
  2. stirringstirred for 30 minutes
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. concentrationconcentrated
  6. customAfter chromatographic purification (silica gel, hexane/ethyl acetate (0-50% ethyl acetate))

Sources & evidence

ORD record
ord-a6cf508775794840b7f8c0ed14c7b53c
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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