3-Methoxypropyne → HCID 66918788, compound

HRID 1367600Notes

Reaction equation

HRID 1367600 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@H:8]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([N:19]=[N+:20]=[N-:21])=[CH:15][C:14]=2[C:22]([F:25])([F:24])[F:23])(=[O:12])=[O:11])[CH2:7][C@@H:6]1[O:26][CH3:27])=[O:4].[CH2:28]([O:31][CH3:32])[C:29]#[CH:30]>C(Cl)Cl.[Cu]I>[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@H:8]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:30]=[C:29]([CH2:28][O:31][CH3:32])[N:21]=[N:20]3)=[CH:15][C:14]=2[C:22]([F:23])([F:24])[F:25])(=[O:12])=[O:11])[CH2:7][C@@H:6]1[O:26][CH3:27])=[O:4]

Participants

5

Reactant 2

HCID 693933-MethoxypropyneHCID 86649035HCID 86649035, compound

Product 1

HCID 66918788HCID 66918788, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,2R,4R) and (1S,2S,4S)-4-(4-azido-2-trifluoromethyl-benzenesulfonyl)-2-methoxy-cyclopentanecarboxylic acid methyl ester (100 mg, 0.245 mmol) in DCM (5 ml) was added methyl propargyl ether (26 mg, 0.371 mmol) and CuI (20 mg, immobilized on Amberlyst A-21, loading 1.2 mmol CuI/g, prepared according to Org. Letters 2006, 8, 1689) and the mixture was placed on a shaker over night. The mixture was then filtered and concentrated and the remaining oil was purified by silica gel chromatography (DCM/MeOH 98:2) to obtain the title compound (62 mg, 53%) as colorless oil. MS (EI): 478.1 (M+H)+.

Workup

  1. waitthe mixture was placed on a shaker over night
  2. filtrationThe mixture was then filtered
  3. concentrationconcentrated
  4. customthe remaining oil was purified by silica gel chromatography (DCM/MeOH 98:2)

Sources & evidence

ORD record
ord-58a866fc16634144a6cd84f1423ab646
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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