Methanol → Methyl (R)-3-(N-Cyclohexyl-N-n-propylamino)-8-fluoro-3,4-dihydro-2H-1-benzopyran-5-carboxylate

HRID 52284Notes

Reaction equation

HRID 52284 reaction equation
[CH:1]1([N:7]([C@@H:11]2[CH2:16][C:15]3[C:17](OS(C(F)(F)F)(=O)=O)=[CH:18][CH:19]=[C:20]([F:21])[C:14]=3[O:13][CH2:12]2)[CH2:8][CH2:9][CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:37][OH:38].[C]=O.CN([CH:44]=[O:45])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:1]1([N:7]([C@@H:11]2[CH2:16][C:15]3=[C:17]([C:37]([O:45][CH3:44])=[O:38])[CH:18]=[CH:19][C:20]([F:21])=[C:14]3[O:13][CH2:12]2)[CH2:8][CH2:9][CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 53638232HCID 53638232, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 54503847Methyl (R)-3-(N-Cyclohexyl-N-n-propylamino)-8-fluoro-3,4-dihydro-2H-1-benzopyran-5-carboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 812191,3-Bis(diphenylphosphino)propaneCatalystHCID 167845palladium(II) acetateCatalyst

Procedure

(R)-3-(N-Cyclohexyl-N-n-propylamino)-8-fluoro-5-trifluoromethylsulfonyloxy-3,4-dihydro-2H-1-benzopyran (0.8 g, 1.8 mmol) (4), DMF (30 mL), triethylamine (0.5 g, 5 mmol), methanol (0.8 g, 13 mmol), palladium(II)acetate (30 mg, 0.14 mmol) and 1,3-bis(diphenylphosphino)propane (60 mg, 0.14 mmol) were placed in a round-bottomed flask. The solution was stirred at 75° C. in an atmosphere of carbon monoxide for 4 h. After evaporation of the solvent in vacuo and subjecting the crude to flash chromatography, 0.6 g (76% yield) of the title compound as a colorless oil was isolated. GC/MS (70 eV) M=349 (30 %).

Workup

  1. customAfter evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-3a6c3dbf6754455198e60a41e52839a2
Source dataset
uspto-grants-1997_04
Patent number
US05616610

Reaction notes

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