Nanofin → HCID 21836512, compound

HRID 1739747Notes

Reaction equation

HRID 1739747 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10](OS(C)(=O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH:26]([CH3:30])[NH:25]1>C(=O)(O)[O-].[Na+]>[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10]([N:25]3[CH:26]([CH3:30])[CH2:27][CH2:28][CH2:29][CH:24]3[CH3:23])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 68843NanofinHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 21836512HCID 21836512, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

1-Diphenylmethyl-3-methanesulphonyloxyazetidine (see Preparation 54) (2 g, 1 mol. equiv.) and 2,6-dimethylpiperidine (6.79 ml, 3 mol. equiv.) were heated together at 110° C. under nitrogen for six hours. Saturated aqueous sodium bicarbonate solution (60 ml) was added and the mixture extracted with ethyl acetate (3×40 ml). The combined organic extracts were dried using magnesium sulphate. The organic solvent was removed under reduced pressure and the residue purified by flash column chromatography on silica gel eluting with methanol:dichloromethane (1:9, by volume) to give the title compound (0.48 g). TLC Rf=0.39 (silica, methanol:dichloromethane, 1:9, by volume). LRMS m/z=335 (m+1)+. Found: C, 80.29; H, 9.00; N, 8.14. C23H30N2 0.125 CH2Cl2 requires C, 80.48; H, 8.84; N, 8.12%.

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×40 ml)
  2. customThe combined organic extracts were dried
  3. customThe organic solvent was removed under reduced pressure
  4. customthe residue purified by flash column chromatography on silica gel eluting with methanol:dichloromethane (1:9, by volume)

Sources & evidence

ORD record
ord-57f0379365174b8caa3ace0576416c12
Source dataset
uspto-grants-1999_10
Patent number
US05968923

Reaction notes

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