Potassium Carbonate → HCID 86597540, compound

HRID 1296271Notes

Reaction equation

HRID 1296271 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:31][CH2:30][N:11]2[C:12](=[O:29])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16]([C:19]#[C:20][Si](C)(C)C)=[CH:15][C:14]=3[C:25]([F:28])([F:27])[F:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)C1OC=CC=1)CCC.C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:31][CH2:30][N:11]2[C:12](=[O:29])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16]([C:19]#[CH:20])=[CH:15][C:14]=3[C:25]([F:27])([F:28])[F:26])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 43936882-(Tributylstannyl)furanHCID 68687554HCID 68687554, compound

Product 1

HCID 86597540HCID 86597540, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-9-trimethylsilylethynyl-7-trifluoromethyl-pyrazino[2,1-a]isoindol-6(2H)-one, prepared according to procedures described in Example 29 with substitution of tributyl(trimethylsilylethynyl)tin for 2-(tributylstannyl)furan (44 mg, 0.1 mmol in MeOH (1.0 mL) was added potassium carbonate (13 mg, 0.1 mmol). The reaction was stirred for 5 min and then quenched with brine. The reaction was extracted with EtOAc (2×5 mL). The organic layers were combined, dried over Na2SO4, and conc. in vacuo to a pale yellow oil. The oil was purified by radial chromatography (silica gel, 30% EtOAc in hexanes) to give 27 mg of the desired-product as a pale yellow oil. MS (ESI) 381 (M+H).

Workup

  1. customquenched with brine
  2. extractionThe reaction was extracted with EtOAc (2×5 mL)
  3. dry with materialdried over Na2SO4
  4. customThe oil was purified by radial chromatography (silica gel, 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f1bf1bedc3ff4472a0d8b5182adc9c6c
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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