Sodium hydride → HCID 19605421, compound

HRID 1603650Notes

Reaction equation

HRID 1603650 reaction equation
[CH2:1]([S:8][CH:9]1[NH:12][C:11](=[O:13])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:16]1([CH2:22][CH2:23][CH2:24]OS(C(F)(F)F)(=O)=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[CH2:1]([S:8][CH:9]1[N:12]([CH2:24][CH2:23][CH2:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11](=[O:13])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 13452363HCID 13452363, compoundHCID 19605253HCID 19605253, compound

Product 1

HCID 19605421HCID 19605421, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4-(benzylthio)azetidin-2-one (1.1 g, 5.5 mmol) in dry THF (10 ml) was added dropwise over 10 minutes to a suspension of NaH (0.13 g, 5.6 mmol) in dry THF (5 ml) at -20° C. under a N2 atmosphere. A solution of 3-phenyl-1-(trifluoromethanesulfonyloxy)propane (1.5 g, 5.6 mmol) in dry THF (10 ml) was added dropwise over 10 minutes at -55° C. After stirring for 1 hour, the mixture was poured into ice/water (50 g), filtered through hyflo, the THF evaporated under reduced pressure and the residue taken up in ethyl acetate. The solution was washed with brine (×2), dried (MgSO4), evaporated under reduced pressure and purified by flash chromatography on silica gel eluted with 5:1 petroleum ethemethyl acetate to give the title compound as a yellow oil (1.4 g, 81%). 1H NMR δ (CDCl3) 2.58 (2H, m, CH2), 2.58 (2H, t, J=15 Hz, CH2Ph), 2.9, 3.2 (each 2H, m, H-3 & NCH2), 3.73 (2H, s, SCH2), 4.51 (1H, m, H-4), 7.2 (10H, m, 2×Ph--H)

Workup

  1. filtrationfiltered through hyflo
  2. customthe THF evaporated under reduced pressure
  3. washThe solution was washed with brine (×2)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. custompurified by flash chromatography on silica gel
  7. washeluted with 5:1 petroleum ethemethyl acetate

Sources & evidence

ORD record
ord-f5f2fb47969e44b5acf8801b6baf3ece
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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