Potassium Carbonate → HCID 67073265, compound

HRID 2252979Notes

Reaction equation

HRID 2252979 reaction equation
C[O:2][C:3]1C=CC(C[C@H]2OCCNC2)=C[CH:4]=1.[C:16]([N:23]1[CH2:28][CH2:27][O:26][C@H:25]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32](I)[CH:31]=2)[CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+].C([Sn](CCCC)(CCCC)C(OCC)=C)CCC>[Cl-].C([N+](CC)(CC)CC)C.CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:16]([N:23]1[CH2:28][CH2:27][O:26][C@H:25]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([C:3](=[O:2])[CH3:4])[CH:31]=2)[CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 67073032HCID 67073032, compoundHCID 67073220HCID 67073220, compound

Product 1

HCID 67073265HCID 67073265, compound

Reagents, catalysts & solvents 3

HCID 5946Tetraethylammonium ChlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (61 mg, 0.053 mmol) was added to a solution of intermediate (b), N-Boc-(R)-2-(3-Iodo-4-methoxybenzyl)morpholine (229 mg, 0.529 mmol), potassium carbonate (146 mg, 1.058 mmol), tetraethylammonium chloride (88 mg, 0.529 mmol) and tributyl(1-ethoxyvinyl)tin (0.179 mL, 0.529 mmol) in N,N-dimethyl formamide and heated to 90° C. for 18 h. The cooled reaction mixture was filtered and the liquors partitioned between ethyl acetate and water. The organic phase was separated and dried (Na2SO4) and concentrated to give the crude product which was purified by silica gel chromatography (silica: 10% ethyl acetate:dichloromethane) affording the crude material (a), N-Boc-(R)-2-(3-acetyl-4-methoxybenzyl)morpholine as a brown oil (248 mg) that was used without further purification.

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. customthe liquors partitioned between ethyl acetate and water
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give the crude product which
  8. customwas purified by silica gel chromatography (silica: 10% ethyl acetate:dichloromethane)

Sources & evidence

ORD record
ord-9041db0523804da5a0b874cbf617d9bd
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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