Potassium Carbonate → HCID 53469198, compound

HRID 573805Notes

Reaction equation

HRID 573805 reaction equation
C([O:4][C@H:5]1[C:14]2[N:13]=[C:12]([CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:11]3[C@@H:21]([C:28]4[CH:33]=[CH:32][C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][CH:29]=4)[O:22][C:23]4([CH2:27][CH2:26][CH2:25][CH2:24]4)[C:10]=3[C:9]=2[C@@H:8]([O:38][Si](C(C)(C)C)(C)C)[CH2:7][C:6]1([CH3:47])[CH3:46])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)C>[C:34]([C:31]1[CH:32]=[CH:33][C:28]([C@@H:21]2[C:11]3[C:12]([CH:15]4[CH2:16][CH2:17][O:18][CH2:19][CH2:20]4)=[N:13][C:14]4[C@H:5]([OH:4])[C:6]([CH3:47])([CH3:46])[CH2:7][C@H:8]([OH:38])[C:9]=4[C:10]=3[C:23]3([CH2:24][CH2:25][CH2:26][CH2:27]3)[O:22]2)=[CH:29][CH:30]=1)([CH3:35])([CH3:36])[CH3:37]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 66762201HCID 66762201, compound

Product 1

HCID 53469198HCID 53469198, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

17 mg (3′R,6′R,9′S)-9′-(tert-butyldimethylsilyloxy)-3′-(4-tert-butylphenyl)-7′,7′-dimethyl-4′-(tetrahydro-2H-pyran-4-yl)-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]-6′-yl acetate are dissolved in 1 ml methanol and treated with 200 mg potassium carbonate. The mixture is stirred for 36 hours at room temperature, diluted with diethylether and washed with water and saturated aqueous sodium bicarbonate. The organic phase is dried with magnesium sulphate and the solvent is evaporated in vacuo. The residue is chromatographed on silica gel (petrole ether/ethylacetate 80:20 to 40:60).

Workup

  1. washwashed with water and saturated aqueous sodium bicarbonate
  2. dry with materialThe organic phase is dried with magnesium sulphate
  3. customthe solvent is evaporated in vacuo
  4. customThe residue is chromatographed on silica gel (petrole ether/ethylacetate 80:20 to 40:60)

Sources & evidence

ORD record
ord-cca53cbeaa83433fb17305d55a564e4b
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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