1,4-Butanesultam → HCID 57634651, compound

HRID 2109848Notes

Reaction equation

HRID 2109848 reaction equation
[C:1]([N:4]1[CH:9]([CH2:10]OCC2C=CC=CC=2)[CH2:8][N:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:6](=[O:27])[CH2:5]1)(=[O:3])[CH3:2].[S:28]1(=[O:35])(=[O:34])[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]1.C(C=P(CCCC)(CCCC)CCCC)#N>C(O)C.C1C=CC=CC=1.[Pd]>[C:1]([N:4]1[CH:9]([CH2:10][N:29]2[CH2:30][CH2:31][CH2:32][CH2:33][S:28]2(=[O:35])=[O:34])[CH2:8][N:7]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[C:6](=[O:27])[CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 3035081,4-ButanesultamHCID 4622928CyanomethylenetributylphosphoraneHCID 576346344-Acetyl-5-[(benzyloxy)methyl]-1-(4-fluorobenzyl)piperazin-2-one

Product 1

HCID 57634651HCID 57634651, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

A mixture of 4-acetyl-5-[(benzyloxy)methyl]-1-(4-fluorobenzyl)piperazin-2-one (6.5 g) and 20% Pd/C (1.4 g) in ethanol (175 mL) was shaken under an atmosphere of hydrogen (60 psi) at room temperature overnight. The product mixture was filtered through a pad of Celite, and concentrated under vacuum. Residual ethanol was removed by co-evaporation with toluene under vacuum (3×). The resultant alcohol was used without further purification. A mixture of the alcohol (1.0 g, 3.57 mmol), 1,2-thiazinane 1,1-dioxide (0.73, 5.4 mmol), and cyanomethylenetri-n-butylphosphorane (1.3 g, 5.4 mmol; [157141-27-0]) in benzene (20 mL) was purged with nitrogen and heated in a sealed tube at 100° C. overnight. The reaction mixture was concentrated under vacuum, and the residue was subjected to column chromatography on silica gel eluting with a mixture of 5% methanol in ethyl acetate. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. filtrationThe product mixture was filtered through a pad of Celite
  2. concentrationconcentrated under vacuum
  3. customResidual ethanol was removed by co-evaporation with toluene under vacuum (3×)
  4. customThe resultant alcohol was used without further purification
  5. customwas purged with nitrogen
  6. temperatureheated in a sealed tube at 100° C. overnight
  7. concentrationThe reaction mixture was concentrated under vacuum
  8. additionthe residue was subjected to column chromatography on silica gel eluting with a mixture of 5% methanol in ethyl acetate
  9. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-185bef652ae444d9a15218efd159e3e2
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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