Methanol → HCID 54532856, compound

HRID 52281Notes

Reaction equation

HRID 52281 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-3,4-dihydro-2H-1-benzopyran (3.7 g, 8.7 mmol), DMF (50 mL), triethylamine (2.5 g, 25 mmol), methanol (4 g, 130 mmol), palladium(ll)acetate (100 mg, 0.45 mmol) and 1,3-bis(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-2f9f55238b704974972030b3c51a0f9a
Source dataset
uspto-grants-1997_04
Patent number
US05616610

Reaction notes

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