Methanol → HCID 54532856, compound

HRID 1738325Notes

Reaction equation

HRID 1738325 reaction equation
[CH:1]1([N:6]([C@@H:10]2[CH2:15][C:14]3[C:16](OS(C(F)(F)F)(=O)=O)=[CH:17][CH:18]=[C:19]([F:20])[C:13]=3[O:12][CH2:11]2)[CH2:7][CH2:8][CH3:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:36][OH:37].[C]=O.CN([CH:43]=[O:44])C>C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:1]1([N:6]([C@@H:10]2[CH2:15][C:14]3=[C:16]([C:36]([O:44][CH3:43])=[O:37])[CH:17]=[CH:18][C:19]([F:20])=[C:13]3[O:12][CH2:11]2)[CH2:7][CH2:8][CH3:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 22871222HCID 22871222, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 54532856HCID 54532856, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 812191,3-Bis(diphenylphosphino)propaneCatalyst

Procedure

(R)-3-(N-Cyclopentyl-N-n-propylamino)-8-fluoro-5-trifluoromethylsulfonyloxy-3,4dihydro-2H-1-benzopyran (3.7 g, 8.7 mmol), DMF (50 mL), triethylamine (2.5 g, 25 mmol), methanol (4 g, 130 mmol), palladiuma(II)acetate (100 mg, 0.45 mmol) and 1,3bis(diphenylphosphino)propane (200 mg, 0.48 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, 2.5 g (86 % yield) of the title compound as a colorless oil was isolated. GC/MS (70 eV) M=335 (20 %).

Workup

  1. customAfter evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-d565c1e879984f39a8bfa99ed43b8bec
Source dataset
uspto-grants-1999_10
Patent number
US05962514

Reaction notes

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