HCID 12400364, compound → HCID 19766133, compound

HRID 1591047Notes

Reaction equation

HRID 1591047 reaction equation
[C:1]1([C:7]2[S:13][CH2:12][CH2:11][NH:10][C:9](=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[C:1]1([C:7]2[S:13][CH2:12][CH2:11][NH:10][CH2:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 12400364HCID 12400364, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19766133HCID 19766133, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

3,4-Dihydro-7-phenyl-1,4-thiazepin-5(2H)-one (3.30 g, 16.2 mm cl) is added to 50 mL of absolute diethyl ether. The reaction mixture is then cooled to 0° C. and lithium aluminum hydride (16.7 mL of a 1M ethereal solution) is added. The reaction mixture is then stirred overnight at room temperature and is quenched by the addition of 2.5 mL of water followed by 5 mL of 10% aqueous sodium hydroxide solution. The solids are filtered and washed with absolute ethanol. The filtrates are combined and concentrated under reduced pressure and the resulting residue is chromatographed on silica eluting with 10:1 dichloromethane:methanol to obtain 1.63 g of the product as a clear oil.

Workup

  1. customis quenched by the addition of 2.5 mL of water
  2. filtrationThe solids are filtered
  3. washwashed with absolute ethanol
  4. concentrationconcentrated under reduced pressure
  5. customthe resulting residue is chromatographed on silica eluting with 10:1 dichloromethane

Sources & evidence

ORD record
ord-bb2a9b8863cd45eeb3214fba8a8e5f58
Source dataset
uspto-grants-1993_04
Patent number
US05206233

Reaction notes

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