1,2-Epoxy-3-methoxypropane → HCID 58494657, compound

HRID 516230Notes

Reaction equation

HRID 516230 reaction equation
[CH2:1]([C:3]1[C:4]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13][C:5]=2[CH:6]=[C:7]2[C:12]=1[NH:11][CH2:10][CH2:9][CH2:8]2)[CH3:2].[CH2:25]([O:29][CH3:30])[CH:26]1[O:28][CH2:27]1.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.C(=O)(O)[O-].[Na+]>C(#N)C.CCOC(C)=O>[CH2:1]([C:3]1[C:4]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:14][CH2:13][C:5]=2[CH:6]=[C:7]2[C:12]=1[N:11]([CH2:27][CH:26]([OH:28])[CH2:25][O:29][CH3:30])[CH2:10][CH2:9][CH2:8]2)[CH3:2]

Participants

7

Reactant 4

HCID 135891,2-Epoxy-3-methoxypropaneHCID 516892Sodium BicarbonateHCID 2733225Ytterbium triflateHCID 66982109HCID 66982109, compound

Product 1

HCID 58494657HCID 58494657, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 140 mg of t-butyl 11-ethyl-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate in 1.86 ml of acetonitrile was added 0.12 ml of glycidylmethylether, followed by substitution with argon. In an ice-bath, 9 mg of ytterbium(III) trifluoromethanesulfonate was added thereto, followed by stirring at room temperature for 2 hours, then elevating the temperature to 50° C., and stirring overnight. To the reaction mixture were added EtOAc and aqueous sodium bicarbonate, and the organic layer was washed with water and saturated brine. The solvent was evaporated under reduced pressure and the resulting residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 147 mg of t-butyl 11-ethyl-1-(2-hydroxy-3-methoxypropyl)-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate.

Workup

  1. customto 50° C.
  2. stirringstirring overnight
  3. washthe organic layer was washed with water and saturated brine
  4. customThe solvent was evaporated under reduced pressure
  5. customthe resulting residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-a2397d40a49749438dc6a957b43c8190
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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